STEREOSPECIFIC SYNTHESIS OF DIVINYL SELENIDES. NUCLEOPHILIC SUBSTITUTIONS OF UNACTIVATED VINYL HALIDES BY VINYL SELENIDE ANIONS

Article abstract of DOI:10.1016/S0040-4020(01)87402-0

Vinyl alkyl selenides can be dealkylated by nucleophilic substitution or by electron transfer to give vinyl selenide anions which retain the configuration of the starting products.The same anions are also produced by electron transfer from vinyl acetyl selenides.The vinyl selenide anions react with vinyl halides, in DMF or DMA, to give divinyl selenides.These reactions occur with retention of configuration and present a new example of nucleophilic substitutions of unactivated vinyl halides.