350-56-1Relevant articles and documents
NUCLEOPHILIC REACTIONS AT A VINYL CENTER. XXIII. REACTIONS OF BROMOFLUOROETHYLENES WITH SODIUM BENZENETHIOLATE
Shainyan, B. A.,Bel'skii, V. K.
, p. 2096 - 2101 (2007/10/02)
The reactions of a number of bromofluoroethylenes with sodium benzenethiolate were investigated.The reactions go regioselectively.The phenylthio group adds to the carbon linked to a fluorine atom.With CF2=CHBr the addition product PhSCF2CH2Br is formed.The alkene CHBr=CHF does not react with PhSNa even after prolonged boiling in ethanol.The alkene CBr2=CHF gives a 1:2 mixture of the Z and E isomers of PhSCF=CHBr.The composition of the products of the reaction of PhSNa with the Z and E isomers of CFBr=CHBr depends on its isomeric composition.The Z isomer gives the product of nucleophilic vinyl substitution with the preservation of the configuration, the Z isomer of PhSCF=CHBr, whereas the E isomer gives products of halophilic reduction, PhSCF=CH2 and PhSSPh, and in smaller amounts also products of vinyl substitution both with the preservation, but also with the inversion, of the configuration, the Z and E isomers of PhSCF=CHBr.The alkene CFBr=CBr2 reacts smoothly to give only the product of nucleophilic vinyl substitution, PhSCF=CBr2.All the sulfides obtained were oxidized to sulfones.The structures of the compounds were established by means of 1H, 13C, and 19F NMR and, in the case of the E isomer of PhSO2CF=CHBr by x-ray structure analysis.
