STEREOSPECIFIC SYNTHESIS OF DIVINYL DISELENIDES FROM VINYL ACETYL SELENIDES

Article abstract of DOI:10.1016/S0040-4020(01)87301-4

Vinyl halides react with MeSeLi in DMF to afford vinyl methyl selenides which are demethylated by the excess of the MeSeLi; the vinyl selenide anions thus obtained react with acetyl chloride to give vinyl acetyl selenides.This three steps one pot synthesis occurs with complete retention of configuration.The vinyl acetyl selenides are cleanly fragmented by electron transfer to the vinyl selenide anions; addition of iodine to the resulting solutions produced the divinyl diselenides with retention of configuration.The transformation of vinyl acetyl selenides into divinyl diselenides can also be induced by catalytic amounts of a solution of sodium in HMPA or of sodium methanethiolate.