Preparation and regioselective reactions of novel gem-difluorinated vinyloxiranes with some organometallic reagents.
Hitherto unknown, relatively labile gem-difluorinated vinyloxiranes were prepared by difluoro-Wittig reactions with alpha,beta-epoxyketones; for these vinyloxiranes alkyl groups were delivered at the fluorine-attached terminal carbon atom in an SN2' manner by RLi, while Me3Al and MeMgBr-CuCl (3: 1) introduced the Me group at the allylic epoxy carbon with retention and inversion of the original stereochemistry, respectively.
Chemistry of fluorinated enamines. Novel reaction of trifluoromethylated enamine with grignard reagents
Abstract Trifluoromethylated enamine, N -(2,3,3,3-tetrafluoro-1-propenyl)dimethylamine ( 1 ), readily reacted with a variety of Grignard reagents 2 at room temperature to afford the trifluorovinyl compounds 3 in good yields.
A convenient synthesis of perfluoroalkylated enamines and vinyl phosphonates
Abstract The reaction of fluoroalkynes with ammonia and benzylamine gave perfluoroalkylated enamines predominantly as the Z isomer, which were hydrogenated with palladium on carbon to afford perfluoroalkylated β -amino acids in good yield. The reaction of fluoroalkynes with diethyl phosphite afforded perfluoroalkylated vinyl phosphonates in moderate yield.