USE OF MOIST SILICA GEL FOR OBTAINING α-ETHYLENIC CARBONYL COMPOUNDS FROM Β-ALKYLTHIO OR β-PHENYLTHIO ALLYLIC ALCOHOLS.

Article abstract of DOI:10.1016/S0040-4020(01)86148-2

The β-alkylthio and β-phenylthio α-ethylenic aldehydes 2, (Z)-6, (E)-6 and 9 were obtained from the corresponding β-chloro α-ethylenic aldehydes, and the α-phenylthiometylidene ketones (Z)-13 and (E)-13 by Peterson reaction with α,α-dimethoxycyclohexanone followed by deacetalization.Reduction (NaBH4) or addition of organolithium compounds led to allylic alcohols which gave α-ethylenic carbonyl compounds with removal of thiol or thiophenol after treatment by moist acidic silica gel with or without mercuric chloride.The method also worked for oxygenated compounds 21, 22.