page_title: Plumbylene
section_title: Synthesis
hierarchical_section_title: Plumbylene / Synthesis
caption_attribution_description: English: General synthesis of plumbylenes
context_page_description: Plumbylenes are divalent organolead(II) analogues of carbenes, with the general chemical formula, R₂Pb, where R denotes a substituent. Plumbylenes possess 6 electrons in their valence shell, and are considered open shell species.
  The first plumbylene reported was the dialkylplumbylene, [(Me₃Si)₂CH]₂Pb, which was synthesized by Michael F. Lappert et al in 1973.
  Plumbylenes may be further classified into carbon-substituted plumbylenes, plumbylenes stabilized by a group 15 or 16 element, and monohalogenated plumbylenes.
context_section_description: Plumbylenes can generally be synthesized via the transmetallation of PbX₂ (where X denotes halogen) with an organolithium (RLi) or Grignard reagent (RMgX). The first reported plumbylene, [((CH₃)₃Si)₂CH]₂Pb, was synthesized by Michael F. Lappert et al by transmetallation of PbCl₂ with [((CH₃)₃Si)₂CH]Li. The addition of equimolar RLi to PbX₂ produces the monohalogenated plumbylene (RPbX); addition of 2 equivalents leads to disubstituted plumbylene (R₂Pb). Adding an organolithium or Grignard reagent with a different organic substituent (i.e. R’Li/R’MgX) from RPbX leads to the synthesis of heteroleptic plumbylenes (RR’Pb). Dialkyl-, diaryl-, diamido-, dithioplumbylenes, and monohalogenated plumbyelenes have been successfully synthesized this way.
  Transmetallation with [((CH₃)₃Si)₂N]₂Pb as the Pb(II) precursor has also been used to synthesize diarylplumbylenes, disilylplumbylenes, and saturated N-heterocyclic plumbylenes.
  Alternatively, plumbylenes may be synthesized from the reductive dehalogenation of tetravalent organolead compounds (R₂PbX₂).
caption: General synthesis of plumbylenes via transmetallation
exif: {}