Synthesis of Conjugated Diallenes by Double [2,3]-Sigmatropic Rearrangement of Conjugated Diyne Trichloromethanesulfenates

Abstract

The preparation of several 2,4-diyne-l,6-diols and their esterification with trichloromethanesulfenyl chloride is described. The thus generated bis-propargylic trichloromethanesulfenates undergo spontaneous double [2,3]-sigmatropic rearrangement which leads to the formation of conjugated diallenic trichloromethyl sulfoxides in good to excellent yields.