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The synthesis of mechanically interlocked molecules has progressed significantly since early reports.1,2 This was largely made possible by the development of passive template methodologies, inspired by Sauvage and co-workers' seminal work,3 in which non-covalent interactions direct mechanical bond formation.4 Thus, there exists a range of methodologies for the synthesis of complex interlocked structures in excellent yield in the mechanical bond-forming step.
The contrast in efficiency between the synthesis of the macrocycle and the formation of the mechanical bond is perhaps nowhere more acute than in our small bipyridine macrocycle modification14 of Leigh's active template Cu-mediated alkyne-azide cycloaddition15 (AT-CuAAC)16 reaction.17,18 Although AT-CuAAC reactions with small bipyridine macrocycles have been described as “amongst the highest yielding and readily accessible routes to stable interlocked structures”,4c the synthesis of the macrocyclic bipyridine precursor is extremely inefficient, proceeding in just 4–11% yield. Given the proven utility of the AT-CuAAC reaction for the synthesis of functionalised rotaxanes,14a,19 including examples with multiple mechanical bonds,14d,20 stabilised organometallic species,14b stereochemically complex interlocked molecules,14c interlocked catalysts,9g and molecular machines,6a the limitations placed on the application of this powerful methodology by the poor availability of the most efficacious macrocyclic precursors19 is a significant barrier to further developments.
Here we report an operationally simple method for the scalable synthesis of bipyridine macrocycles from readily available substrates that effectively removes this limitation. All of the bipyridine macrocycles reported are efficiently converted to rotaxanes under standard conditions. We demonstrate the long term potential of the AT-CuAAC approach with these now readily available substrates through the gram-scale synthesis of a rotaxane catalyst precursor, and a novel synthesis of Sauvage-type molecular shuttles.
Bipyridine macrocycles suitable for AT-CuAAC reactions such as 2a are typically synthesised via a double Williamson cyclisation of a pre-formed bipyridine precursor.14,16b,21 However, the preferred trans-rotamer of the bipyridine unit22 disfavours the desired cyclisation, leading to low yields, particularly in the case of smaller macrocycles.23 To overcome this, we resolved to form the ligand during the macrocyclisation reaction.
Previous routes to bipyridine macrocycles have made use of the Ni-mediated reductive coupling24 of 2-halo pyridines25 to produce the bipyridine moiety prior to the macrocyclisation step.14,16b Although Ni-mediated couplings have not been employed as a macrocyclisation reaction for the preparation of bipyridine macrocycles for incorporation into interlocked architectures,26 similar reactions have been successful in the key cyclisation step towards cyclic and bicyclic oligoparaphenylenes,27,28 as well as limited examples of bi-phenyl and bi-benzyl natural products.29 Accordingly, dibromo precursor 1a was synthesised from known intermediates in a succinct manner (see ESI†) and, under high dilution, subjected to conditions based on those developed by the groups of Tiecco and Iyoda for the Ni-mediated intermolecular homo-coupling of 2-halo-pyridines.25a,c No reaction was observed (Table 1, entry 1).
a Reagents and conditions: 0.1 mmol each 1a, NiII, NEt4I, 0.4 mmol PPh3 in total, DMF, 50 °C, 4 h. b Determined by 1H NMR analysis of the crude product. c 5 mM conc. of 1a. d 0.05 M conc. of 1a. e Pseudo-high dilution (4 h addition, 0.05 M final conc. of 1a). f THF as solvent. n.r. = no reaction.
1c NiCl2·6H2O Zn (2) n.r.
Repeating the same reaction at higher concentration (entry 2) led to consumption of 1a to give 2a, albeit in low yield. Combining these observations, slow addition of 1a to the preformed Ni0 species under otherwise identical conditions gave macrocycle 2a in 37% yield (entry 3). A brief screen of reaction conditions revealed that replacing NiCl2·6H2O with NiBr2(PPh3)2 resulted in an increased yield of 2a (entry 4), whereas conducting the reaction in THF, commonly employed in such couplings,25a led to a less efficient reaction (entry 5). Increasing the equivalents of Zn reduced the yield of product, with significant proto-dehalogenation observed in the crude mixture (entry 6). On the hypothesis that this was due to halogen–zinc exchange competing with the desired Ni-mediated process, Mn was substituted for Zn leading to an improved yield (entry 7).30 Finally, increasing the equivalents of Mn (entry 8) to improve the efficiency of reductive steps during the catalytic cycle,24 gave 2a in 70% yield.
Under our optimised conditions, the preparative scale (2 mmol) reaction of 1a provided macrocycle 2a in an excellent 71% isolated yield (Fig. 1) and so we extended our investigation to a selection of previously reported and novel macrocycles. An ether link proximal to the pyridine unit did not affect the outcome; previously disclosed macrocycles 2b and 2c were produced in excellent yields, demonstrating that, unlike Williamson ether methods, the Ni-mediated cyclisation is relatively insensitive to ring size. Furthermore, when the dichloro analogue of 1b was employed, macrocycle 2b was produced in 56% yield, indicating that 2-chloro pyridines are also viable substrates. The reaction also tolerates heteroatom substitution on the pyridine ring (2d) although in this case an elevated temperature was required due to the lower reactivity of the more electron-rich substrate.31 Similarly, the reaction tolerates 6-aryl-substitution; sterically hindered macrocycle 2e, a smaller analogue of Sauvage's iconic phenanthroline macrocycle,3 was produced in excellent 73% yield.
Fig. 1 Synthesis of macrocycles 2 at 2 mmol scale. aReaction conditions as in Table 1, entry 8. bMacrocyclisation yield of the best previous synthesis. cT = 70 °C. dSolvent = DMF–THF (3 : 1). eYield from Br/I precursor.
We then extended the Ni-mediated coupling to the synthesis of unsymmetrical bipyridine macrocycles, important intermediates in the synthesis of mechanically chiral molecules.14c Macrocycle 2f, a hybrid of macrocycles 2a and 2b in which the two pyridine moieties are differentiated by a proximal ether unit, was produced in excellent 76% yield. Initial attempts to extend our approach to previously disclosed macrocycle 2g were hampered by the poor solubility of 1g in DMF. This was readily overcome by employing a DMF–THF solvent mixture, leading to 2g in 66% yield, an order of magnitude improvement over the previous synthesis (4%). When the flexible alkyl chain of 2g was replaced by a p-xylyl moiety to give 2h, the yield of the macrocyclisation reaction fell to 41%, presumably due to the increased strain of the smaller, more rigid macrocycle. However, the yield of 2h remains significantly higher than previous syntheses (6%; see ESI†) and demonstrates that the Ni-coupling can be used to generate more challenging structures.
Finally, we extended our approach to an aryl-pyridine cross-coupling. Initial attempts with the corresponding dibromo precursor delivered 2i in a low 16% yield. However, replacing the bromo-benzene moiety with an iodo-benzene starting material raised the yield to 24%, suggesting that there is potential to extend our efficient Ni-mediated ring closure to other biaryl macrocyclic motifs in future.
The Ni-mediated synthesis of bipyridine macrocycles is obviously a dramatic improvement over established procedures in terms of simple reaction yield, by as much as an order of magnitude in some cases. Other key benefits of this methodology include: (i) the Ni-mediated coupling appears relatively insensitive to substrate structure (ring size, pyridine substituents) and tolerates simple modifications (temperature, solvent) where required; (ii) the reaction is capable of producing unsymmetrical bipyridine macrocycles such as 2f–i through a formal intramolecular cross-coupling reaction; (iii) bis-halopyridine precursors 1 are readily available on scale using simple chemistry and commercially available precursors; (iv) isolation of the product is simplified both by the improved impurity profile of the crude product and by the use of pseudo-high dilution conditions.
This latter point renders the Ni-mediated macrocyclisation highly scalable; whereas previous syntheses of small bipyridine macrocycles 2a, 2b, 2g and 2h required between 3 and 9 litres of DMF per mmol of product, only ∼30 ml of DMF is required to produce each mmol of macrocycle using the method presented here. Using James' EMAC measure of reaction efficiency,13 a logarithmic scale taking into account the yield and reaction concentration, this corresponds to an increase in reaction efficiency from EMAC = 3 to 7. Furthermore, the excellent reaction yield is maintained across a range of scales; repeating the synthesis of 2a (Scheme 1) with 5 mmol of 1a delivered 1.6 g of macrocycle 2a (69% isolated yield).
Scheme 1 Large scale macrocyclisation and AT-CuAAC reactions. aConditions as Table 1, entry 8. b[Cu(MeCN)4](PF6), NiPr2Et, CH2Cl2–EtOH (1 : 1), 80 °C, 18 h.
Furthermore, with significant quantities of macrocycles 2 in hand we were able for the first time to demonstrate the scalability of the AT-CuAAC reaction. Previous reports have been limited to small scales (typically 0.025 mmol) by the availability of the macrocycle component. Pleasingly, when the synthesis of interlocked phosphine oxide 5, an advanced precursor of a stimuli-responsive interlocked Au catalyst,9g was carried out at an 80-fold larger scale using 0.96 g of macrocycle 2a (2 mmol) the isolated yield of the interlocked product was increased relative to our previous report, delivering 1.8 g (95%) of 5 in a single synthetic operation.
Now that bipyridine macrocycles are far more readily available their application in more complex mechanically interlocked molecules and molecular machines is a far more attractive proposition. To capitalise on this, we developed a streamlined synthesis of two Sauvage-type molecular shuttles using macrocycles 2a and 2e and compared their behaviour. Such shuttles are usually based on phenanthroline macrocycles and a thread containing a terpyridine and a bipyridine station, assembled using a passive template threading approach.3c Replacing the phenanthroline macrocycle with its bipyridine analogue and the terpyridine and bipyridine stations with bistriazolylpyridine (btp) and monotriazolylpyridine (mtp) units respectively,33,34 greatly facilitates shuttle synthesis using an AT-CuAAC approach. Thus, shuttles 9a and 9e were synthesised in a concise manner from readily available ethynyl pyridine derivatives 6 and 8 through sequential CuAAC couplings of 1,6 bis-azido hexane, delivering 9a and 9e in 73% and 52% isolated yields respectively in the mechanical bond-forming step (Scheme 2).35 The corresponding non-interlocked thread was also synthesised for comparison. With shuttles 9 in hand, we examined their co-conformational behaviour by 1H and ROESY NMR (Fig. 2 and ESI respectively†).
Scheme 2 The AT-CuAAC synthesis and operation of bi-stable molecular shuttles 9. Reagents and conditions: (i) [Cu(MeCN)4](PF6), CH2Cl2, rt; (ii) 2a or 2e [Cu(MeCN)4](PF6), NiPr2Et, CH2Cl2, 80 °C; (iii) [Cu(MeCN)4](PF6), CDCl3; (iv) Zn(OTf)2, CDCl3. R = 3,5-di-tBu-C6H3.
Fig. 2 Partial 1H NMR (500 MHz, CDCl3) of (a) 9a + Zn(OTf)2; (b) 9a + [Cu(MeCN)4](PF6); (c) 9a; (d) non-interlocked thread; (e) 9e; (f) 9e + [Cu(MeCN)4](PF6); (g) 9e + Zn(OTf)2. Selected signals assigned with labels as in Fig. 1 (macrocycle) and Scheme 2 (thread).
Analysis of shuttles 9a and 9e by 1H NMR (Fig. 2c and e respectively) suggests that in both cases the macrocycle predominantly occupies the tridentate btp station; significant shifts of thread triazole protons Hp and Ht were observed relative to the non-interlocked thread (Fig. 2d), whereas protons associate with the bidentate mtp unit remain largely unaffected by the formation of the mechanical bond. ROESY NMR analysis supports this assignment with cross-peaks observed between macrocycle protons and Hq, Hr and Hs of the thread. Given the significant shifts of protons Hp and Ht and our previous observation of C–H⋯N hydrogen bonding in AT-CuAAC derived rotaxanes,14a the localisation of the macrocycle over the btp station in rotaxanes 9 is tentatively attributed to the presence of two C–H⋯N hydrogen-bonding interactions compared with only one in the case of the mtp station.
The behaviour of shuttle 9e proved to be more complicated. Surprisingly, addition of CuI led to the formation of two new species in an approximate 2 : 1 ratio (Fig. 2f). Two-dimensional exchange spectroscopy (2D-EXSY)37 confirmed that these co-conformational isomers are in slow exchange on the NMR timescale with a unimolecular rate constant at room temperature of the order of 10−3 s−1 corresponding to an activation barrier of ∼21 kcal mol−1. The major co-conformation was assigned as that in which the macrocycle, as initially expected, is localised over the bidentate mtp station, based on the shielding of signals corresponding to He, Hd and Hc, and ROESY cross-peaks between HD and HE of the macrocycle and He and Hd of the thread.
Similar analysis confirmed that the minor co-conformation is that in which the macrocycle unexpectedly coordinates the CuI ion at the nominally tridentate btp station, initially suggestive of a five-coordinate Cu centre. However, Schmittel and co-workers have previously reported the formation of a heteroleptic CuI complex derived from one tridentate and one bidentate ligand in which the metal ion adopts the expected four-coordinate geometry, with the fifth donor not involved in binding to the metal ion.38 Although this phenomenon requires further investigation, we tentatively suggest that similar behaviour may account for the minor co-conformation of [Cu(9a)](PF6), with subtle differences in the secondary interactions (C–H⋯π, π⋯π) between macrocycles 2a or 2e and the thread accounting for the differences observed.
Finally, replacing CuI with ZnII led to a much simpler outcome; a single new species was observed with 1H and ROESY NMR confirming that, in the case of the ZnII complex [Zn(9e)](OTf)2, the macrocycle was located predominantly on the tridentate btp station, as expected (Fig. 2g).
In conclusion we have presented an extremely efficient, scalable and general Ni-mediated method for the synthesis of small bipyridine macrocycles for the AT-CuAAC reaction in high yield from readily available precursors under pseudo high dilution conditions. Although this preliminary study has focussed on macrocycles similar to those used previously in the AT-CuAAC reaction, Ni-mediated couplings are typically tolerant to a wide range of functional groups24b and investigations are currently underway to determine the wider substrate scope. These now readily available macrocycles are proven versatile intermediates for the synthesis of interlocked molecules in excellent yield using both active14,16b,18a–e and passive39 template methods. Given the scalability of both the macrocycle synthesis and the mechanical bond forming step demonstrated here, and the clear potential to extend the approach to more complex molecules, the AT-CuAAC reaction mediated by bipyridine macrocycles clearly has a bright future in the synthesis of interlocked architectures for a variety of applications.
We thank Fluorochem for the gift of reagents, the EPSRC National Mass Spectrometry Service for HRMS analysis and the EPSRC (EP/L016621/1), Queen Mary, University of London and the University of Southampton for funding. JEML is a European Commission Marie Skłodowska-Curie Fellow. SMG is a Royal Society Research Fellow. This project has received funding from the European Union’s Horizon 2020 research and innovation programme under the Marie Sklodowska-Curie grant agreement No 660731.
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For medium-ring cyclic bipyridines synthesised under reductive coupling conditions see: (a) C. Botteghi, A. Schionato and O. De Lucchi, Synth. Commun., 1991, 21, 1819–1823 CrossRef CAS ; (b) B. Milani, E. Alessio, G. Mestroni, E. Zangrando, L. Randaccio and G. Consiglio, J. Chem. Soc., Dalton Trans., 1996, 1021–1029 RSC ; (c) J. Durand, E. Zangrando, C. Carfagna and B. Milani, Dalton Trans., 2008, 2171–2182 RSC ; (d) T. R. Kelly, Y. Lee and R. J. Mears, J. Org. Chem., 1997, 62, 2774–2781 CrossRef CAS PubMed .
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Mn has previously been shown not to undergo direct halogen metal exchange processes under similar conditions. See: D. A. Everson, R. Shrestha and D. J. Weix, J. Am. Chem. Soc., 2010, 132, 920–921 CrossRef CAS PubMed .
At 50 °C a significant quantity of the dimeric product was isolated and characterised. See ESI†.
In the case of 2d an excess of half-threads was required. In the case of more rigid, hindered macrocycle 2h a less sterically hindered benzylic azide was required. See ESI for full details†..
For recent reviews on triazole-based ligands see: (a) H. Struthers, T. L. Mindt and R. Schibli, Dalton Trans., 2010, 39, 675 RSC ; (b) J. D. Crowley and D. A. McMorran, Top. Heterocycl. Chem., 2012, 28, 31 CAS ; (c) B. Schulze and U. S. Schubert, Chem. Soc. Rev., 2014, 43, 2522 RSC ; (d) J. P. Byrne, J. A. Kitchen and T. Gunnlaugsson, Chem. Soc. Rev., 2014, 43, 5302 RSC .
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Shuttle 9a was isolated in 73% yield in 95% purity. An analytical sample for use in shuttling experiments was obtained by subjecting a portion of this material to a second round of column chromatography.
The use of CuI and ZnII allows the co-conformational behaviour of 9a and 9e to be monitored readily and in detail by NMR. However, as Sauvage previously reported,3c although the ZnII ion can be removed readily, more forcing conditions (e.g. KCN) are required in the case of CuI. Thus although these systems behave as molecular switches, the reversible switching process itself is somewhat cumbersome. We are currently investigating the in situ electrochemical switching (CuI → CuII) behaviour of such shuttles and these results will be reported in due course.
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text:
Haryana Financial Corporation Vs. Gurcharan Singh & ANR.
2. M/s Amrit Steel Industries, Jagadhari, a proprietorship concern of which the first respondent is the sole proprietor, had obtained a loan of Rs.5,05,750/- on 15.9.1994 from the Appellant, Haryana Financial Corporation, by entering into hypothecation of machinery, fixture, as well as, personal guarantee bond dated 15.9.1994. The first respondent also gave a written undertaking dated 5.3.1994 that he would not dispose of his properties during the currency of the loan. The first respondent failed to repay the loan. Consequently, the Corporation took over the hypothecated property and sold the same and appropriated the amount.
In the meantime, the second respondent, the wife of the first respondent filed Civil SuitNo.767 of 1995 against the first respondent before the Court of Civil Judge(Jr. Divn.), Jagadhari, seeking a declaration that she is the absolute owner and in possession of the properties mentioned in the undertaking dated 5.3.1994. The suit was decreed on 3.2.1996 as against the first respondent.
3. The Corporation then filed Civil Suit No.167 of 2003 in the Court of Additional Civil Judge (Senior Division), Jagadhari, against the Respondents seeking a declaration that the decree dated 3.2.1996 was null and void. The Corporation also submitted that the decree was obtained by fraud to defeat the personal undertaking executed by the first respondent on 5.3.1994 in favour of the Corporation. The Court decreed the suit holding that the decree passed in Civil Suit No.767 of 1995 is a collusive one obtained to defeat the undertaking created by the first respondent on5.3.1994 in favour of the Corporation.
The second respondent filed Civil Appeal No.34 of 2005 in the Court of Additional District Judge, Yamunanagar. The Additional District Judge, however, allowed the Appeal vide judgment dated 30.8.2005 holding that the loan taken by the first respondent was not subject to charge over the property covered by the decree in Civil Suit No.767 of 1995 and that the Appellant had no locus standi to challenge the decree suffered by the first respondent in favour of the second respondent. The Corporation aggrieved by the aforesaid judgment filed RSA No.44 of 2006 before the Punjab and Haryana High Court, which was dismissed by the High Court on 9.1.2006. Aggrieved by the same, the Corporation has filed the present Appeal.
4. Shri Amit Dayal, learned counsel appearing for the Corporation, submitted that the High Court has committed an error in sustaining the order passed by the Additional District Judge after having found that the decree obtained by the second respondent against the first respondent in Civil Suit No.167 of 2003 was a collusive one. Learned counsel submitted that apparently such a decree was obtained without any contest by the first respondent, only to defeat the undertaking given to the Corporation on 5.3.1994.
Learned counsel also placed reliance on the judgments of this Court in S.P. Cheranalvaraya Naidu (dead) by LRs. v. Jagannath (dead) by LRs and others [(1994) 1 SCC 1] and Badami (deceased) by her LR v. Bhali[(2012) 11 SCC 574] and submitted that the Court cannot grant relief to a party who has obtained a fraudulent decree and who has come to the Court with unclean hands. Learned counsel also placed reliance on the judgment of this Court in M.L. Abdul Jabbar Sahib v. M.V. Venkata Sastri & Sons & Ors. [(1969) 1 SCC 573] and submitted that even if the undertaking dated5.3.1994 was not registered, still the first respondent is bound by the undertaking and the Corporation can always proceed against the properties referred to in the said undertaking.
5. Shri Gagan Gupta, learned Advocate appearing for the Respondents, submitted that the High Court has rightly affirmed the judgment of the lower Appellate Court after having noticed that the undertaking dated5.3.1994 has not created any charge over the properties mentioned therein. Consequently, the Corporation cannot proceed against the properties mentioned in the undertaking.
Learned counsel submitted that without transfer of interest in the properties in question by a registered document, no charge could be created in those properties and hence the Corporation cannot proceed against those properties on the basis of mere undertaking dated 5.3.1994. In support of this contention, reliance was placed on the judgments of this Court in K. Muthuswami Gounder v. N.Palaniappa Gounder [(1998) 7 SCC 327] and Bank of India v. Abhay D.Narottam and others [(2005) 11 SCC 520].
I, Gurcharan Singh, the above named deponent do hereby verify contents of the above paras as true and correct to the best of my knowledge and belief and nothing has been concealed from.
Further confirm that the means as indicated above in the name shall not be disposed off during the currency of the loan.
7. The above-mentioned undertaking dated 5.3.1994 was submitted by the first respondent on a duly attested Stamp Paper, but was not registered under the Registration Act. The above-mentioned undertaking was given before the loan was sanctioned to the first respondent on 15.9.1994. We also fully endorse the view taken by the Courts below that the decree in Civil Suit No.767 of 1995 was obtained by the second respondent as against the first respondent collusively to defeat the undertaking given by the first respondent on 5.3.1994 in favour of the Corporation. Still the question is whether the undertaking dated 5.3.1994 has created any charge over the properties mentioned therein in favour of the Corporation.
This Court in J.K. (Bombay) Private Limited v. New Kaiser-I-Hind Spinning & Weaving Co. Ltd. & Others [(1969) 2 SCR 866], explained the difference between the charge and the mortgage as follows :- "While in the case of a charge there is no transfer of property or any interest therein, but only the creation of a right of payment out of the specified property, a mortgage effectuates transfer of property or an interest therein. No particular form of words is necessary to create a charge and all that is necessary is that there must be a clear intention to make a property security for payment of money in praesnti."
2) Charges arising by operation of law.
9. An ordinary charge created under the Transfer of Property Act is compulsorily registerable. The first portion of Section 100 of the TP Act lays down that where immoveable property of one person is by act of parties or operation of law made security for the payment of money to another, and the transaction does not amount to a mortgage, the latter person is said to have a charge on the property; and all the provisions herein before contained which apply to a simple mortgage shall, so far as may be, apply to such charge.
The words "which apply to a simple mortgage shall, so far as may be, apply to such charge" in this Section were substituted by Section 53 of the Transfer of Property (Amendment) Act, 1929, for the words" as to a mortgagor shall, so far as may be, apply to the owner of such property, and the provisions of Sections 81 and 82 shall, so far as may be, apply to the persons having such charge." Evidently, the effect of the amendment was that all the provisions of the TP Act which apply to simple mortgages were made applicable to charges.
10. Section 59 of the Transfer of Property Act refers to the mode of transfer which reads as follows :- "59. Mortgage when to be by assurance.- Where the principal money secured is one hundred rupees or upwards, a mortgage other than a mortgage by deposit of title- deeds can be effected only by a registered instrument signed by the mortgagor and attested by at least two witnesses. Where the principal money secured is less than one hundred rupees, a mortgage may be effected either by a registered instrument signed and attested as aforesaid, or (except in the case of a simple mortgage) by delivery of the property."
11. A conjoint reading of Section 100 with Section 59 of the TP Act makes it clear that if by act of parties, any immovable property is made security for the payment of money to another and it does not amount to mortgage, then all the provisions which apply to a simple mortgage, as far as may be, apply to such charge. Consequently, in view of Section 59 of the TP Act when there is a mortgage other than a mortgage by deposit of the title deeds, it can be effected only by a registered instrument. So far as the present case is concerned, no registered mortgage deed was executed by the first respondent and no title deed of the property was handed over by the first respondent to the Corporation.
"17. The document, Exhibit A-6, security bond does not in substance offer suit property by way of security. Even giving the most liberal construction to the document, we cannot say that a charge as such has been created in respect of the suit property for money to be decreed in the suit. All that it states is that in the event of a decree being passed not to alienate the property till the decree is discharged, which is a mere undertaking without creating a charge. Therefore, we agree with the finding of the High Court that the document at Exhibit A-6 is not a charge. If that is so, the suit filed by the appellant has got to be dismissed."
12. The Court held that the decree obtained in that suit was a simple money decree and not a decree on a charge or mortgage with the result that the appellant who purchased the property in execution of that decree did not acquire the rights under the Security Bond.
13. In Bank of India (supra), this Court was examining the scope of undertaking made for creating an equitable charge over a flat in favour of the Bank. This Court held that without a transfer of interest, there is no question of there being a mortgage and that mere undertaking is not sufficient to create a charge. The ratio laid down by the above-mentioned judgment applies to the present case. In our view, the mere undertaking that the party will not dispose of the properties mentioned in an undertaking, during the currency of the loan, will not create any charge over those properties, unless charge is created by deposit of title deeds or through a registered document.
We also hold that even if the purpose of the decree obtained in Civil Suit No.767 of 1995 between the respondents was fraudulent and collusive one so to defeat the undertaking made on 5.3.1994, that would not confer any charge over the properties, unless the undertaking is registered. We, therefore, find no error in the judgment of the lower Appellate Court which was affirmed by the High Court.
14. In the result, the appeal fails and is accordingly dismissed. There will be no order as to costs.

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§ 171-1 Adoption of Code.
§ 171-2 Code supersedes prior ordinances.
§ 171-4 Copy of Code on file.
§ 171-5 Amendments to Code.
§ 171-7 Code book to be kept up-to-date.
§ 171-8 Altering or tampering with Code; penalties for violation.
§ 171-9 Severability of Code provisions.
§ 171-10 Severability of ordinance provisions.
§ 171-11 Repeal of ordinances.
§ 171-12 Ordinances saved from repeal.
§ 171-13 Changes in previously adopted ordinances.
Pursuant to N.J.S.A. 40:49-4, the ordinances of the Board of Health of the Township of Harmony of a general and permanent nature, as revised, codified and consolidated into chapters and sections by General Code Publishers Corp., and consisting of Chapters 171 through 185, are hereby approved, adopted, ordained and enacted as the "Code of the Township of Harmony," hereinafter known and referred to as the "Code."
All provisions of this ordinance and the Code shall take effect thirty (30) days after the date of the first publication.
A copy of the Code in loose-leaf form has been filed in the office of the Secretary of the Board of Health and shall remain there for use and examination by the public until final action is taken on this ordinance; and, if this ordinance shall be adopted, such copy shall be certified as provided by law, and such certified copy shall remain on file in the office of the Secretary of the Board of Health, to be made available to persons desiring to examine the same during all times while said Code is in effect.
Any and all additions, amendments or supplements to the Code, when passed and adopted in such form as to indicate the intent of the Board of Health to make them a part thereof, shall be deemed to be incorporated into such Code so that reference to the "Code of the Township of Harmony" shall be understood and intended to include such additions and amendments. Whenever such additions, amendments or supplements to the Code shall be adopted, they shall thereafter be printed and, as provided hereunder, inserted in the loose-leaf book containing said Code, as amendments and supplements thereto.
It shall be unlawful for anyone to improperly change or amend, by additions or deletions, any part or portion of the Code, or to alter or tamper with such Code in any manner whatsoever which will cause the law of the Board of Health to be misrepresented thereby. Anyone violating this section of this ordinance shall be subject, upon conviction, to a fine of not less than five dollars ($5.) nor more than five hundred dollars ($500.).
Each section of the Code and every part of each section is an independent section or part of a section, and the holding of any section or a part thereof to be unconstitutional, void or ineffective for any cause shall not be deemed to affect the validity or constitutionality of any other section or part thereof.
Any ordinance of the Board of Health adopted subsequent to December 7, 1988.
In compiling and preparing the ordinances of the Board of Health for adoption and revision as part of the Code pursuant to N.J.S.A. 40:49-4, certain grammatical changes and other minor changes were made in one (1) or more of said ordinances. It is the intention of the Board of Health that all such changes be adopted as part of the Code as if the ordinances so changed had been previously formally amended to read as such.
Editor's Note: Pursuant to § 171-13B, the following sections were amended: §§ 176-4 and 185-9. A complete description of these changes is on file in the office of the Secretary of the Board of Health.


Justia › US Law › Case Law › New York Case Law › New York Appellate Division, First Department Decisions › 2012 › Fletcher v Dakota, Inc.
Fletcher v Dakota, Inc. 2012 NY Slip Op 05338 Decided on July 3, 2012 Appellate Division, First Department Acosta, J. Published by New York State Law Reporting Bureau pursuant to Judiciary Law § 431. This opinion is uncorrected and subject to revision before publication in the Official Reports.
Dakota, Inc., et al., Defendants-Appellants, Pamela Lovinger, et al. Defendants.
Defendants The Dakota, Inc., Bruce Barnes and Peter Nitze appeal from an order of the Supreme Court, New York County (Eileen A. Rakower, J.), entered July 27, 2011, which, insofar as appealed from, denied their motion to dismiss the first, second and fifth through eleventh causes of action as against The Dakota, the first and sixth through eleventh causes of action as against Barnes in his individual capacity, and the first and fifth causes of action as against Nitze in his individual capacity.
York (Milton L. Williams, Jr.
Kasowitz, David E. Ross, Trevor J.
Plaintiff Alphonse Fletcher, Jr., an African-American resident of defendant co-op The Dakota, alleges that The Dakota and, as relevant to this appeal, two of its directors (defendants Barnes and Nitze) discriminated against him, inter alia, on the basis of race in refusing to approve his purchase of an apartment adjacent to one he owns for the purpose of combining the two. According to Fletcher, the case is about retaliation against him for sticking up for the rights of others, including minority and Jewish shareholders and applicants at The Dakota, and then to further defame him when he brought the discriminatory conduct to light.
Prior to discussing the relevant causes of action, we address individual board member liability in the context of discriminatory acts, and clear up an element of possible confusion in this area of law that may arise out of this Court's decision in Pelton v 77 Park Ave. Condominium (38 AD3d 1 ). In short, although participation in a breach of contract will typically not give rise to individual director liability, the participation of an individual director in a corporation's tort is sufficient to give rise to individual liability.
Turning to the contentions on appeal, defendants argue that all claims should be dismissed as against Nitze and Barnes because the complaint fails to allege that they engaged in any acts separate and distinct from actions they took as board members. The claims that remain as against Nitze that we must address are breach of fiduciary duty (first cause of action) insofar as it is based on allegations of defamation, and defamation (fifth cause of action). As to Barnes, the remaining causes of action are the first insofar as it is based on defamation, the sixth and eighth, which allege discrimination under the New York State and City human rights laws, the seventh and ninth, which allege retaliation in violation of the State and City human rights laws, respectively, the tenth, which alleges a violation of the Civil Rights Law, and the eleventh, which alleges tortious interference with contract. Since defendants are not challenging the motion court's ruling that the discrimination-based claims (the sixth, eighth and tenth) otherwise fail to state a cause of action, but only that they fail to allege independent conduct on Barnes's part, we begin with those claims.
The provisions of the State Human Rights Law (State HRL) that proscribe discrimination in housing apply not only to the "owner" of the housing, but also to a "lessee, sub-lessee, assignee, or managing agent of, or other person having the right to sell, rent or lease a housing accommodation . . . or any agent or employee thereof" (Executive Law § 296[a]). The City Human Rights Law (City HRL) similarly provides for individual liability (Administrative Code of the City of NY § 8-107). Although both statutes contain exceptions to their housing coverage (compare Exective Law § 296[a]) with Administrative Code of the City of NY §§ 8-107[a], [g]-[m],[o]), there are no exemptions in either statute for directors or officers of a coop or any other corporation. The anti-retaliation sections of both statutes also provide for [*3]individual liability with no exemption for corporate directors or officers (see Executive Law § 296; Administrative Code of the City of NY § 8-107)[FN1]. Individual director and officer liability is also consistent with the limitations on the "business judgment" rule as enunciated by the Court of Appeals.
In Matter of Levandusky v One Fifth Ave. Apt. Corp. (75 NY2d 530), the Court of Appeals held that the "business judgment" rule was the correct standard of judicial review of the actions of the directors of a cooperative corporation. That rule prohibits judicial inquiry into the actions of corporate directors taken in good faith and in the exercise of honest judgment in the lawful and legitimate furtherance of corporate purposes" (id. at 537-538 [internal quotation marks omitted]). The Court, however, cautioned that "the broad powers of a cooperative board hold potential for abuse through arbitrary and malicious decision making, favoritism, discrimination and the like" (id. at 536). In 40 W. 67th St. v Pullman (100 NY2d 147, 157 ), the Court of Appeals "reaffirm[ed] [Levandusky's] admonition and stress[ed] that those types of abuses are incompatible with good faith and the exercise of honest judgment. While deferential, the Levandusky standard should not serve as a rubber stamp for cooperative board actions" (emphasis added). Thus, arbitrary or malicious decision making or decision making tainted by discriminatory considerations is not protected by the business judgment rule.
Nothing in the holding or reasoning of either Levandusky or Pullman suggests that there is a safe harbor from judicial inquiry for directors who are alleged to have engaged in conduct not protected by the business judgment rule. Moreover, there is no principle of corporate law that director liability arises only where the director commits a tort independent of the tort committed by the corporation itself. On the contrary, it has long been held by this Court that "a corporate officer who participates in the commission of a tort may be held individually liable, . . . regardless of whether the corporate veil is pierced" (Peguero v 601 Realty Corp., 58 AD3d 556  [internal quotation marks omitted], quoting Espinosa v Rand, 24 AD3d 102, 102 , quoting American Exp. Travel Related Services Co., Inc. v North Atlantic Resources, Inc., 261 AD 2d 310, 311 ; Savannah T & T Co., Inc. v Force One Express Inc., 58 AD3d 409 ; cf. Polonetsky v Better Homes Depot, 97 NY2d 46, 55  ["In actions for fraud, corporate officers and directors may be held individually liable if they participated in or had knowledge of the fraud, even if they did not stand to gain personally"]; Marine Midland Bank v Russo Produce Co., 50 NY2d 31, 44 , citing Lippman Packing Corp. v Rose, 203 Misc 1041, 1044 , which noted, even then, that "a long list of cases . . . ha[d] . . . held that the officers, directors and agents of a corporation are jointly and severally liable for torts committed [*4]on behalf of a corporation and the fact that they also acted on behalf of the corporation does not relieve them from personal liability"]).
A leading treatise on corporations states that a director may be held individually liable to third parties for a corporate tort if he either participated in the tort or else directed, controlled, approved, or ratified the decision that led to the plaintiff's injury" (see 3A Fletcher Cyclopedia of the Law Corporations § 1135). This rule protects individual board members who did not participate or aid and abet the tortfeasors from being held vicariously liable for the tortfeasors' action.
Nevertheless, defendants contend that this Court's decision in Pelton v 77 Park Ave. Condominium (38 AD3d 1 ) requires that the discrimination claims be dismissed as against Barnes. In Pelton, the plaintiff brought a disability discrimination claim, under the City HRL, against his condominium and the individual members of the board of managers based on their alleged failure to properly accommodate his disability. This Court granted summary judgment dismissing the action against the individual board members, reasoning that (1) the Levandusky standard was not satisfied, and (2) the plaintiff failed to allege "independent tortious conduct" by the individual defendants "in order to overcome the public policy that supports the business judgment rule" (id. at 10). However, there are two problems with this reasoning. First, as discussed above, the Levandusky rule will not protect a board member where he engages in discriminatory conduct. Second, Pelton takes a rule that applies where a cooperative or condominium board is alleged to have breached a contractual obligation, and incorrectly applies it where a board allegedly engaged in the intentional tort of discrimination. That is, Pelton failed to disentangle the principles of individual corporate director liability in the breach of contract context (understood to provide a shield against liability) from the principles applicable to tort cases (where there is no such shield). As authority for our holding in Pelton, we cited Murtha v Yonkers Child Care Assn. (45 NY2d 913 ). We now find, however, that our reliance on Murtha was misplaced, and we therefore decline to follow, and expressly overrule, the pleading rule articulated in Pelton.
Murtha is a breach of contract case in which the Court of Appeals stated that a corporate officer will not be held liable for inducing the breach of a contract between the corporation and a third party if he committed no "independent torts or predatory acts" (45 NY2d at 915). The Court had no occasion to hold, or even suggest that a director would not be held liable for a tort committed by the corporation if he had not committed a tort independent of that tort. In Brasseur v Speranza (21 AD3d 297 ), which the Pelton Court cited as an example of a Murtha pleading failure, we dismissed a breach of fiduciary duty claim against individual board members because "there is no allegation that they breached a duty other than, and independent of, those contractually imposed upon the board" (id. at 298 [emphasis added]). Moreover, we find that the Pelton pleading rule conflicts with Court of Appeals' warning that discrimination, among other abusive practices, is not protected by the business judgment rule (see Levandusky, 75 NY2d at 536; Pullman, 100 NY2d at 157). It also is inconsistent with the Court of Appeals' recent instruction that "we must construe Administrative Code § 8-107(7), like other provisions of the City's Human Rights Law, broadly in favor of discrimination plaintiffs, to the extent that such a [*5]construction is reasonably possible" (Albunio v. City of New York, 16 NY3d 472, 477-78 ). Thus, we decline to dismiss the sixth, eighth and tenth causes of action as against defendant Barnes.
Defendants contend that the retaliation claims (the seventh and ninth causes of action) should be dismissed as against The Dakota and Barnes for failure to state a cause of action. The State HRL provides in, pertinent part, that "[i]t shall be . . . unlawful . . . to retaliate . . . against any person because he or she has opposed any practices forbidden under this article . . ." (Executive Law § 296). To make out a claim of retaliation under the State HRL, the complaint must allege that (1) Fletcher engaged in a protected activity by opposing conduct prohibited there under; (2) defendants were aware of that activity; (3) he was subject to an adverse action; and (4) there was a causal connection between the protected activity and the adverse action (Forrest v Jewish Guild for the Blind, 3 NY3d 295, 312-313 ).
The City HRL provides in, pertinent part, that "[i]t shall be . . . unlawful . . . to retaliate . . . in any manner against any person because such person has . . . opposed any practice forbidden under this chapter" (Administrative Code § 8-107). "The retaliation . . . complained of under this subdivision need not result in an ultimate action . . . or in a materially adverse change . . . [but] must be reasonably likely to deter a person from engaging in protected activity" (id.).
In interpreting the City HRL, we start from the premise that the Local Civil Rights Restoration Act requires that "we . . . construe Administrative Code § 8-107(7), like other provisions of the City's Human Rights Law, broadly in favor of discrimination plaintiffs, to the extent that such a construction is reasonably possible" (Albunio v City of New York, 16 NY3d 472, 477-78 ). "[I]t is important that the assessment [of a retaliation claim] be made with a keen sense of [the] realities [of the circumstances surrounding the plaintiff], of the fact that the "chilling effect" of particular conduct is context-dependent, and of the fact that a jury is generally best suited to evaluate the impact of retaliatory conduct in light of those realities" (Williams v New York City Hous. Auth., 61 AD3d 62, 71 , lv denied 13 NY3d 702  [in the context of a motion for summary judgment]).
The complaint alleges that Fletcher began to oppose discrimination (or conduct that he [*6]perceived as discriminatory) after he was elected president of the coop board in May 2007. In or about September 2007, he complained to defendant Nitze that another board member's reference to certain applicants as "Jewish mafia" was "not appropriate." The applicants were initially rejected, although plaintiff and one other board member voted to approve. He further alleged that, "[a]lthough defendant Nitze tried to persuade Fletcher not to raise the issue again, Fletcher urged the Board to reconsider the couple's application on the record.'" The board granted the couple an interview, after which it approved the application.
Fletcher's protest that the "Jewish mafia" comment and the general tenor of the discussion about the Jewish couple's "ethnicity and religion" were inappropriate constitutes the kind of activity that is protected under the State HRL. Thus, the first element of a retaliation claim was alleged.
The second element was alleged with respect to defendant The Dakota. Since defendant Nitze was a director, his knowledge of Fletcher's activity is imputed to The Dakota (see Baker v Latham Sparrowbush Associates, 72 F3d 246, 255 [2d Cir 1995], citing, inter alia, Matter of Brown, 252 NY 366, 375-378 ; Keen v Keen, 113 AD2d 964, 966 , lv dismissed, 67 NY2d 602 ; Texaco, Inc. v Weinberg, 13 AD2d 1002 ; Richmond Hill Realty Co. v East Richmond Hill Land Co., 246 App Div 301, 305 ). However, Barnes did not become a member of the board until May 2009, and plaintiffs do not allege that he was aware of Fletcher's protected activity. Thus, the seventh and ninth causes of action should be dismissed as against Barnes and the Dakota. However, since discovery may reveal that he was aware of Fletcher's protected activity, the dismissal as against Barnes should be without prejudice.
Plaintiffs' allegations that defendants "denied Fletcher the benefit of having the Transfer Disclosure Policy govern his application to purchase Apartment 50; (b) denied Fletcher the impartial, fair, and unbiased review of his financial disclosures; [and] (c) recommended rejection of Fletcher's application" are sufficient to establish that Fletcher was subjected to an adverse action, and satisfy the third prong of a retaliation claim.
The fourth prong is satisfied by plaintiffs' allegation that defendants took the above mentioned adverse action in retaliation for his efforts to defend victims of discrimination by them (Hicks v Baines, 593 F.3d 159, 170 [2d Cir. 2010]). The fact that the alleged retaliation commenced a substantial period of time after the protected activity was engaged in does not defeat the claim: Fletcher's application for approval to purchase Apartment 50 in the early part of 2010 represented the first opportunity for retaliation (see Bernhardt v Interbank of New York, 2009 WL 255992, at *6, 2009 US Dist. LEXIS 8173, *20 [ED NY 2009]; McKenzie v Nicholson, 2009 WL 179253, *5 n5, 2009 US Dist. LEXIS 5285 [ED NY 2009]; Batyreva v New York City Dep't of Education, 2008 WL 4344583, *14; Quinby v WestLB AG, 2007 WL 1153994,*13, 2008 US Dist LEXIS 28657, *35-39 [SD NY 2007]).
Thus, we decline to dismiss as against The Dakota Fletcher's retaliation claims under the State and City HRLs to the extent they are based on his conduct with respect to the Jewish couple.
The complaint also alleges that Fletcher "made it clear" to the rest of the board that jokes about the number of times a certain shareholder would have to apply to fix her bathroom were [*7]inappropriate. Although the shareholder was African-American, the complaint does not allege that Fletcher made any reference to her race. Thus, it fails to state a cause of action under the State HRL for retaliation on the basis of Fletcher's conduct with respect to this shareholder (see e.g. Forrest, 3 NY3d at 313 [granting defendant summary judgment because "[a]lthough plaintiff filed numerous grievances claiming generalized harassment,' she never alleged that she was discriminated against because of race"]; see Sullivan v Chappius, 711 F Supp 2d 279, 287 [WD NY 2010] [dismissing complaint based on plaintiff's supervisor's extramarital affair]). Thus, the seventh and ninth causes of action should have been dismissed against the Dakota insofar as they are based on Fletcher's conduct with respect to the African-American shareholder. However, the dismissal is without prejudice, because following discovery, plaintiffs may be able to plead further details that would show that Fletcher was engaged in protected activity.
We note that under the City HRL, a jury may infer from other evidence that a plaintiff's activity is in fact opposition to discrimination even where the plaintiff does "not say so in so many words" (see Albunio, 16 NY3d at 479). However, even under the City HRL, a complaint drafted by counsel that contains 269 numbered paragraphs without alleging even on information and belief that defendants knew or should have known that Fletcher was opposing discrimination when he spoke to them about the African-American shareholder who intended to renovate her bathroom fails to state a cause of action for retaliation.
Because The Dakota is a corporation, it owes no fiduciary duty to its shareholders (Peacock v Herald Sq. Loft Corp., 67 AD3d 442, 443 ). Thus, although The Dakota sought to dismiss the first cause of action only to the extent it is based on defamation, we dismiss both the first and second causes of action in their entirety as against The Dakota, because the defectiveness of these claims is "apparent on the face of the record" (see American Bldg. Contrs. Assoc., Inc. v Mica & Wood Creations, LLC., 23 AD3d 322, 323 [internal quotation marks omitted]). Moreover, the dismissal is with prejudice.
As to Barnes and Nitze, they correctly argue that the first cause of action should be dismissed as against them because it fails to adequately plead violations of the individual directors' fiduciary duty (Brasseur v Speranza, 21 AD3d 297, 298 ). However, since discovery may reveal such violations, the dismissal of the first cause of action as against them should be without prejudice.
defamatory statements are pleaded with sufficient particularity (CPLR 3016[a]): "[At an April 14, 2010 board meeting,] one or more of the Individual Defendants told the other members of the Board that Fletcher had not fulfilled binding charitable commitments and pledges, that Fletcher's assets were all illiquid and difficult to value, and that FAM's business loans left it over-extended and at risk of collapse . . ."[On or before May 7, 2010, Nitze told Dakota shareholder Craig Hatkoff that Fletcher] "had not actually given the money he had promised to give [to charity] and he owes it'. . ."[At some point between June 24, 2010 and September 2010] one or more of the Individual Defendants falsely and maliciously stated to Hatkoff that Fletcher had checked out of his business' and was living on borrowed money' . . ."On September 14, 2010, . . . the Board sent a letter to certain Dakota shareholders . . . [It stated, inter alia,] [b]ased on the financial information submitted by Fletcher, the Board concluded that approving such a purchase would not be in the best interest of The Dakota' . . . [The letter] also contained the false and misleading statement that Fletcher had declined the Board's request to provide additional financial information."
While some of these allegations do not specify exactly which of the defendants made a particular statement, that is not a fatal defect (see Torres v Prime Realty Servs., 7 AD3d 343, 344 ; see also Herlihy v Metropolitan Museum of Art, 214 AD2d 250, 260 ).
Defendants further contend that the above-quoted statements are covered by a qualified privilege and that the complaint fails to allege malice sufficient to defeat the privilege (see Liberman v Gelstein, 80 NY2d 429, 437 ). Contrary to the latter contention, the complaint alleges malice. But, in any event, we would not "give conclusive effect to defendants' position of qualified privilege before any affirmative defense to that effect was raised in a responsive pleading" (see Acosta v Vataj, 170 AD2d 348, 348 ). Thus, we decline to dismiss as against The Dakota the fifth cause of action and so much of the first cause of action as it is based on allegations of defamation to the extent they do not rely on statements contained in affidavits.
Contrary to defendants' contention, the tortious interference with contract claim states a cause of action by alleging tortious interference with Fletcher's contract to purchase apartment 50 from Ruth Proskauer Smith's estate (Kronos, Inc. v AVX Corp., 81 NY2d 90, 94 )[FN3]. Thus, we decline to dismiss the eleventh cause of action as against The Dakota. However, it should be dismissed as against Barnes, because the complaint does not allege that Barnes committed independent tortious conduct outside of his role as a board member (see American-European Art Assoc. v Trend Galleries, 227 AD2d 170, 171-172 ). The dismissal is without prejudice since discovery may reveal evidence that would support a claim against Barnes in his individual capacity.
Accordingly, the order of the Supreme Court, New York County (Eileen A. Rakower, J.), entered July 27, 2011, which, insofar as appealed from, denied defendants The Dakota, Inc., Bruce Barnes, and Peter Nitze's motion to dismiss the first, second and fifth through eleventh causes of action as against The Dakota, the first and sixth through eleventh causes of action as against Barnes in his individual capacity, and the first and fifth causes of action as against Nitze in his individual capacity, should be modified, on the law, to dismiss the first cause of action as against The Dakota, with prejudice, and as against Barnes and Nitze, without prejudice; the second cause of action as against The Dakota, with prejudice; so much of the fifth cause of action as is based on statements made in defendants' affidavits, with prejudice; so much of the seventh and ninth causes of action as are based on plaintiffs' conduct with respect to the African-American shareholder who wanted to renovate her apartment as against The Dakota, without prejudice; and the seventh, ninth and eleventh causes of action as against Barnes, without prejudice, and otherwise affirmed, without costs. All concur.
Opinion by Acosta, J. All concur.
Mazzarelli, J.P., Saxe, Catterson, Acosta, Román, JJ.
Footnote 1:The State HRL prohibits retaliation by "any person engaged in any activity to which this section applies" (Executive Law § 296; "[p]erson" includes "one or more individuals" (Executive Law § 292). The City HRL prohibits retaliation by "any person engaged in any activity to which this chapter applies" (Administrative Code § 8-107); "[p]erson" includes "one or more natural persons" (Administrative Code § 8-102).
Footnote 2: While we rely upon Forrest in addressing plaintiff's State HRL claim (because that case continues to be binding upon us in the context of State HRL claims), we do not rely upon Forrest with respect to plaintiff's City HRL claim since the City Council expressly rejected Forrest's application to claims brought under the City HRL when it enacted the Restoration Act (see Bennett, 92 AD3d at 35 n.1, citing, Williams, 61 AD3d at 67).
Footnote 3: We decline to consider defendants' argument that the cause of action fails because the Smith estate did not breached its contract with Fletcher, an element of the cause of action (the estate had the right to cancel the contract if the board refused to approve the sale), because it was raised for the first time in their reply brief.


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Supreme Judicial Court, Superintendence of inferior courts. Practice, Criminal, Speedy trial, Complaint, Dismissal, Interlocutory appeal.
James Rosencranz appeals from a judgment of a single justice of this court denying his petition pursuant to G. L. c. 211, § 3. That petition sought relief from the order of a Boston Municipal Court judge denying Rosencranz’s motion to dismiss a criminal complaint on the ground that he had not been brought to trial within the twelve-month period provided by Mass. R. Crim. P. 36 (b), as amended, 422 Mass. 1503 (1996). The appeal is now before us pursuant to S.J.C. Rule 2:21, as amended, 434 Mass. 1301 (2001). We affirm the judgment of the single justice.
It is established that a defendant in a criminal case is not entitled to appeal from the denial of a motion to dismiss prior to trial. See Jackson v. Commonwealth, 437 Mass. 1008, 1009 (2002). It is also settled that G. L. c. 211, § 3, may not be used to circumvent that rule. Id. “Unless a single justice decides the matter on the merits or reserves and reports it to the full court, neither of which occurred here, a defendant cannot receive review under G. L. c. 211, § 3, from the denial of his motion to dismiss.” Id.
Rosencranz argues that the alleged violation of his right to a speedy trial cannot effectively be remedied through the ordinary appellate process because the pendency of the criminal proceedings in the meantime has ongoing collateral consequences for him; specifically, he contends that the pending case adversely affects his ability to practice law or to secure other employment. We have previously considered and rejected arguments like this. The collateral consequences attendant to the pendency of criminal proceedings — such as “continued anxiety, community suspicion and other social and economic disabilities” — do not necessarily render the regular appellate process inadequate for speedy trial claims. Esteves v. Commonwealth, 434 Mass. 1003, 1003-1004 (2001) (distinguishing speedy trial claims from double jeopardy claims). See Owens v. Commonwealth, 465 Mass. 1010 (2013) (rejecting interlocutory review under G. L. c. 211, § 3, of denial of motion to dismiss based on claim of speedy trial violation); Cousin v. Commonwealth, 442 Mass. 1046 (2004) (same).
Francis J. DiMento, Jr., for the petitioner.
 In a bar discipline proceeding arising out of unrelated events, Rosencranz was suspended from the practice of law in the Commonwealth, effective February 1, 2012, for a period of six months. To date, he has not sought reinstatement.
 We do not address other issues and arguments raised by Rosencranz on appeal that were not raised before the single justice.

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Proportion technique is a realm of “harmonic technique” that appears from the outside to be all numbers and formulae. In spite of this, it is one of the most lively domains, if one starts by understanding the concept of proportion = relationship in terms of its actual nature: an exceptional multitude of possible forms based on principles that are very simple because they are understandable, provable by anyone with basic knowledge, and not very mathematical. In this movement back and forth between numbers, the numbers change into distances and then into tones; thus every individual number, distance, or tone must always somehow agree with two, three, or more others, or else persuade these to agree with it. This process has a seductive charm for those who calculate, draw, and listen along with it; the reader should work over the examples once again and experience them. In this way, he will surely grasp their meaning himself.
In §24a, we discussed proportions while considering “harmonic division-ratios” in the harmonic pencil of rays of the equal-tone lines. Unfortunately, the study of proportion is taught perfunctorily nowadays; textbooks usually devote only a few pages to it, and one wise writer thought that 3-4 pages “might be further abbreviated without repercussions” (Tropfke: Geschichte der Elementarmathematik, 1902, vol. I, p. 232). We shall see about that as we orient ourselves.
This looks very dry. What do these formulae say? First, we will try to clarify them with lines.
i.e. each element of the series is half the sum of its neighbors, e.g.
Now, if we examine our diagram, we immediately notice that in the frequency diagrams, all horizontal rows of the overtone type clearly form continuous arithmetic proportions. This means that every overtone, in terms of its frequency, is half the sum of its two neighboring tones. In the string-length diagram, the “arithmetic” element is in the vertical series.
4 : 8 = 2 : 4 8 · 2 = 4 · 4 16 = 16 etc.
x = √ab (geometric mean).
The median geometric proportion between 2 numbers is the square root of the product of these numbers, which can be demonstrated with our diagram. If a = 3/2 and b = 2/3, then x2 = 3/2 · 2/3 = 1, thus x = 3/2 · 2/3 = √1 = 1. In the diagram, of course, we find other geometric proportions if we merely look for the ratios of equal intervals-for example: 4/2 c : 4/3 f = 2/4 c, : 3/4 g, where the equality-ratio consists of fifths.
Here, as one can see, in contrast with arithmetic proportions, it is not the differences but the ratios of the differences that are equal to the ratios of the two pairs of section differences.
It is now important and interesting to investigate the relationships of the three proportion types to one another. Viewed harmonically, Fig. 179 makes this relationship self-explanatory. In the P-diagram one can draw horizontal, vertical, and perpendicular lines through any point on the generator-tone line to find three intersecting “continuous” arithmetic, harmonic, and geometric proportions in each case-for example, the series through the point 8/8 c, as illustrated in Fig. 179.
The great polarity of major and minor also once again emerges here: all major series (in terms of frequency, as in our diagram) have the arithmetic proportion as a constituent element in the background, and all minor series have the harmonic, whereas the geometric proportion invades them both from one direction and overshoots in the other, holding together the coordinate structure.
For further investigations of the relationships of the three proportion types, their median proportionals are most useful. We find a remarkable conjunction in the circle (Fig. 180); here we also find the solution to the problem of the geometric construction of these three “median” proportionals.
Thus VH must be the harmonic median. VG, the geometric median, results from the right triangle UGW, whose height GV, according to a well-known law of plane geometry, is equal to the square root of the product of the sections that it marks, a and b.
Since, in Fig. 180, point V can be arbitrarily chosen, it is clear that only certain numbers are suited for an “emmelic” ratio of all three median proportionals. What was said in §24a.1 regarding the musical special case of “harmonic proportion” also applies here. We will soon see how the three “medians” relate to one another algebraically and harmonically.
If we now pursue the two halves of this series to the right and left of √2 in the “P” system, we will see that these two halves, 3/2 5/3 9/5 ... and 3/3 3/5 5/9 ... each lie upon a straight line going out from 1/1-a very remarkable condition if we seek the possible “location” of √2, and even more significant if we examine the two end-values which these lines approach, or at which they also finish in the formula, namely α = 1 and ω = 2, as “limits” of these lines. The mathematically adept reader may investigate whether this is true!
We can now operate a three-element continuous proportion with the third proportionals instead of with the median proportionals, to obtain new steps and values. For this proportion technique, which is often important for practical harmonic tasks, one should note the following scheme.
(/10 - /9 - /8).
Thus 25/3 cis is the desired third geometric proportional. In pure tones (without numbers) these are equal intervals, as noted above: i.e. the interval g-e is equal to the interval e-cis (minor thirds). Without arithmetic calculation, then, I could continue the example, saying that the further geometric proportionals to 10 e and 25/3 cis must be ais, since cis-ais is another minor third; and so on.
which to our perception is a B-major (g-minor) scale for a generator-tone of 1/1 c. For the ancient Greeks, however, it was a “Dorian” scale, whose characteristic is that with c as the generator-tone, it begins a whole-tone lower and proceeds like a B-major scale, or with d as the generator-tone, it begins with c and proceeds like C-major. This, of course, only explains it in terms of today's very primitive perception of scales. For the ancient Greeks, and for those nowadays who truly understand “Gregorian chant,” these “church modes” are completely independent sound-forms with different psychical characteristics.
Thimus then continues by differentiating the above proportioning further, and thus comes to a new elicitation of the so-called “enharmonics” of ancient Greek tone-systems that was lost, or at least no longer used, by the later Greeks (Aristoxenos, Ptolemy, etc.): an exquisitely differentiated ratio-construction with deep speculative and symbolic significance.
The reader who, armed with a beginner's background in algebra, calculates the above formulae, works through the proportions, and devotes himself to further related exercises, will certainly appreciate the deeper understanding of the laws of harmonic series-construction thus made possible, despite the apparent schoolbook-like circumstances. In a textbook, these things cannot be ignored. And those for whom such numbers and formulae are an expression of actual relationships, rather than just something external, will share the author's astonishment and wonder at the phenomenon of proportion itself, which is revealed in its innermost nature in the above examples. Especially in the last formula, the inner laws are perceived with redoubled effect. All other readers, though, who follow the suggestion in the preface and skip over the above pages, will be rewarded by the following ektypic excursions.
In his later work Timaeus, Plato ascribes to Timaeus the following words on proportion: “two things cannot be rightly put together without a third; there must be some bond of union between them. And the fairest bond is that which makes the most complete fusion of itself and the things which it combines; and proportion is best adapted to effect such a union.”* And here a definition of geometric proportion is implied: “For whenever in any three numbers, whether cube or square, there is a mean, which is to the last term what the first term is to it; and again, when the mean is to the first term as the last term is to the mean-then the mean becoming first and last, and the first and last both becoming means, they will all of them of necessity come to be the same, and having become the same with one another will be all one.”** (Example: 2/3 f : 1/1 c : 3/2 g, and 1/1 c : 2/3 f = 3/2 g : 1/1). The fact that Plato described the unity of the geometric proportions playing around the generator-tone line as the “fairest bond” is in itself a proof for the “harmonics” of late Platonic thought, a proof that will be further solidified in the harmonic analysis of the scale of the Timaeus (§39).
It is not claiming too much to refer to the phenomenon of ancient Greek thought and perception as a thought and perception in proportions, an ascendance of the spiritual (logos) to a harmonically conditioned interplay of sensuality, in which this proportional relationship (in Greek, in fact, the word for proportion is λόγος = Logos!) plays the role of psychically and spiritually saturated tectonics.
It produces the most important intervallic building blocks: the octave, fifth, fourth, and whole-tone.
The Greeks reached interesting conclusions from the discovery (or rediscovery) of the concept of proportion, only a few of which we can discuss here.
Despite indications in the sources, E. Frank made the old mistake of viewing only the harmonic proportion as musically derivable. The ancients analyzed both the arithmetic and the geometric proportions harmonically, as we saw above; the latter, in fact, does not always need an irrational median or medians. In spite of this, it is indeed the irrational quantity √αω that, to a certain extent, controls and holds together the three harmonic proportions as beginning, end, and middle, and as a secret generating “ineffable” center.
This conclusion, first made possible by harmonic analysis, contradicts the usual opinion of historians wishing to find, in the discovery of irrational numbers, an upheaval of the ancient worldview based only on rational numbers. The exact opposite is the case: the harmonic inclusion of the irrational numbers in the “cosmos” of the being-values arranged between the two infinities (1/∞-1/1-∞/1) strengthens ancient wisdom and perception in the presence of a universal harmony, precisely in that regulating power that grants the irrational numbers their value-emphasized place in the order of things. Of course, the discovery and teaching of proportional methods also had its practical significance. “For the Greeks, the inestimable value of proportions lay in the fact that they presented, with their metamorphoses, a substitute for our equations. This important application explains the extensive treatment given to proportions by the Greek mathematician Euclid (ca. 300 BC), and also by Arabic and Medieval scholars. For a long time in the Middle Ages, and almost up to modern times, when letter notation was finally incorporated into equations, people continued to write the results in the form of proportions, which took the place of our modern closed formulae. Only in modern times has the space allotted to them been severely reduced” (Tropfke: Geschichte der Elementar-Mathematik, 1902, I, p. 232).
From our harmonic viewpoint, we can only agree with these penetrating views. Unfortunately, Stenzel, like all previous philologists, knew only of the periphery of the harmonic backgrounds of Greek thought, and not of the center. The reader who has worked through harmonic fundamentals based on Thimus's studies and this textbook will find hardly anything more depressing than having to look over and work through the forest of often primitive commentary, laboring with insufficient acoustic tools in “dark” numeric-harmonic areas, especially on the fragments of Philolaus, the Pythagoreans in general, and the late philosophy of Plato. If one places all these ideas of the golden age of Greek philosophy upon the background of the concept of akróasis and its norms, its numerically precisely understandable and psychically perceivable laws-a procedure that is not at all arbitrary, but actually encouraged by hundreds of ancient sources-then this “refinement of sensuality,” which Stenzel very rightly detected in those ideas, will become graspable and understandable from a fully new, central position, inwardly adequate to this thought and accessible in the deeper sense to heart and mind. One then sees that Plato did not “come upon the unhappy [!] idea, in his old age, of developing the world of ideas as a number-system” (W. Windelband: Platon, 1905, p. 93). On the contrary, for Plato, number-harmonics was the bond joining idea and sensuality, and it was Windelband himself who came upon a very “unhappy idea.” In my essay on Pythagoras (in Abhandlungen), I attempted for the first time to rectify the most important Pythagorean theorems of akróasis, which indeed place the eye and ear on an equal level with thought. But a harmonic analysis of all Greek philosophy up to around Proclus would require half a life's work; this analysis requires a precise familiarity with the fundamentals of harmonics and an equally great knowledge of philosophical and natural history, supported by thorough language abilities. I am sure that whoever undertakes this project will achieve results that place all of the ancients' scientific, artistic, and philosophical thoughts and experiences upon a new, central foundation, not as seen by our modern thought but self-radiating from the cosmos of Greek thought.
After this digression, we now return to our proportions and will note a few more typical examples for the ektypics of harmonic proportioning.
The twelve sides, eight corners, and six faces of the cube form a harmonic proportion. Nicomachus and Iamblichus believed that on this basis, the ancients spoke of a ̔αρμωνία γεωμετρική (geometric harmony); because the octave (12 : 6 = 2 : 1), the fifth (12 : 8 = 3 : 2), and the fourth (8 : 6 = 4 : 3) are all present in the cube's ratios. As we saw in §24, geometry, through the significance of harmonic proportion, is anchored in harmonics especially on its projective side. Clavius, in his commentary on Euclid, concentrates completely on a musical proportion, which emerges in a triangle M1 M2 M3 that bisects any triangle A B C and the corresponding segments on the connecting lines of the corner points and the bisection points (Fig. 206).
Here I have written all possible proportions between one another, so that his example shows how the material of our partial-tone coordinates, albeit lacking thirds here, emerges from a very simple notation of various proportional possibilities, with an elementary geometric theorem well known to the ancients.
The Pythagorean triangle, with sides 3, 4, and 5, yields a considerably richer psychic harvest.
Since it was traditional for the Greeks to test all segments on the monochord and to set the tone-values obtained in relation to one another, we will set the segment-numbers and their squares together with the corresponding tone-values (since for a right triangle, c2 = a2 + b2).
Unfortunately, the “second part” mentioned by Thimus, i.e. the third volume of his Harmonikale Symbolik, was never published, and so far the search for the supposedly existing manuscript has proved fruitless. The letter from Newton to Harington speaks for itself. If such a great spirit was not afraid to take number-harmonic investigations seriously, and indeed to direct his special attention to them, then this is a challenge and incentive for us today to give a new foundation to the whole field of harmonics and to draw the corresponding conclusions.
Further on in the domain of elementary geometry, there is a wealth of typical harmonic features, especially in the so-called “curious properties of the triangle,” the sections determined by them, and so forth. This is actually expressed in the word “chordal” (from ̔η χορδή = the string), and “hypotenuse” (from ̔υποτείνω = to span, namely a string). The beginnings of the function-concept and the seedlings of analytical geometry are also based on the ancient concept of proportion, whose innermost nature the ancients knew how to derive harmonically and substantiate, as we have seen. The formula for changing a rectangle into a square, which we write today as the formula x2 = ab, was expressed by the Greeks in the proportion a : x = x : b, etc. There is more on this in the textbooks on the history of mathematics cited in the bibliography for this chapter.
It is highly interesting to note the sudden emergence of the imaginary number i when the two division ratios of a harmonically constructed segment are set equal.
From all these examples, and those in §24, it is undoubtedly evident that seen historically, the fundamentals of the “new” projective geometry, the germ of the function-concept, analytical geometry, the concept of the infinite, the irrational, and the imaginary (the number i), are all based on a common denominator of the universal concept of proportion. The fact that the Greeks did not yet need our modern formulae makes no difference regarding the actual knowledge that they obviously possessed about these things. The common view of Greek thought is that it was directed only towards the finite, the “rational”; but for us, from the harmonic standpoint, the derivation and basing of all these very “modern” concepts upon that of harmonic proportion is of exceptional importance. This shows that the concept of the ratio in itself, which indeed is most distinctly characterized in the interval, has a constructive significance in the whole structure of mathematics.
If we grasp the nature of proportion in the value-formal sense, as I tried to do in my Grundriß (p. 277ff. and 280ff.) under the value-forms of “ratio-equalization” and “being-proportion,” this meaning becomes almost universal. The reader should use his own knowledge and experience, and the parts of Grundriß just mentioned, to make up for the lack of space to discuss further ektypic examples here. The “golden section,” harmonically a third-sixth problem, was specially discussed in my Harmonia Plantarum, p. 148ff. In §29.1 and §55.8 we will discuss this further.
From our human viewpoint, the concept of the “relationship” of humans to one another is nothing other than proportions of psychic individualities, whose “tones” must or should be tuned to one another so as to somehow satisfy the proportional relationship, not in a mathematical but in a value sense. Anyone who is comfortable in a circle of friends knows well enough how someone who does not belong in the circle “disturbs” it, which says nothing about the disturber as an autonomous being-value, but simply affirms the fact that the previously existing proportion is no longer in tune when a foreign element is introduced. But a thought that is new, unfamiliar, objectionable, also acts as a power in the previously existing spiritual proportion, and must either adjust to the existing elements (if it is too weak) or else, by the strength of its own value, rectify the other elements until they enter into a new proportion with it.
The domains that emerge in a new light upon the background of harmonic proportions will be discussed later. The first, “harmonics and architecture,” will be the subject of the next chapter. The proportions of the human form will be brought into connection with the “sound-image” in §38, and proportional relationships in the planetary system will appear in §41 with the discussion of the Timaeus scale; further harmonic theorems must be discussed beforehand.
A. von Thimus, Harmonikale Symbolik, preface x ff., I, 118ff., 196ff., II, 32ff. H. Kayser, Hörende Mensch, Ch. 2; Klang, 20, 21, 36, 37, 51-2, 142, 145; Grundriß, 103, 155, 287. On mathematical proportions, see the familiar textbooks. For a new discussion of Greek thoughts and perceptions from the standpoint of akróasis, indispensable initial literary tools are: 1) A. von Thimus, Harmonikale Symbolik; 2) Diels' Fragmente der Vorsokratiker; 3) Grundriß, vol. I; 4) E. Frank, Plato und die sogenannte Pythagoreer, 1923; 5) J. Stenzel, Zahl und Gestalt bei Plato und Aristoteles, 1924; and 6) the author's fundamentals of new harmonics compiled in his works, especially his essay on Pythagoras in Abhandlungen. Aristides Quintilianus's De Musica, fundamental for the entire “atmosphere” of Pythagorean musical philosophy, has been excellently translated into German by R. Schäfke (Berlin 1937). Regarding Frank, the first thing to observe is that the main value of his book is in its wealth of dates and references, and in the fundamentally correct assessment of harmonics in Greek thought. As far as I can see, even specialists reject his quirk of proving that the “so-called” (!) Pythagoreans were mythical. Stenzel's work is valuable as an excellent collection of sources; it also does justice through many subtle and deep thoughts to the assessment of the “harmonic” side of Plato's later philosophy in its numeric-spiritual aspect. But neither Frank nor Stenzel knew that this actually had a technical harmonic background, though Thimus had brought it to light long before them, and for these reasons they often labor vainly with certain things that a harmonic analysis could make very simple. But precisely for this reason, their books are more important for us harmonists; once one has studied through them, one often has the feeling that many false conclusions, incorrect interpretations, and misunderstandings in certain places can be rectified by the single concept of tone-number, not to mention the various harmonic theorems themselves, which often shed a brilliant light in the darkest places.
But above all, the harmonically versed philologist should make a new foray into ancient mathematics, metrics, music theory, and natural philosophy. It seems to me that there is a wealth of harmonic relics here, in manuscripts or in published but little-known authors, with which history not yet known where to start, simply because no one has been able to arrange them into any “valid” science-and thus no one has been interested in them.
* Plato, Timaeus, 31, tr. by Benjamin Jowett.