Tetrahedron

Stereospecific synthesis of 1, 5-dien-3-ynes and 1, 3, 5-trienes application to the stereochemical identification of trienic sex pheromones

F Tellier, C Descoins, R Sauvêtre

Index: Tellier, Frederique; Descoins, Charles; Sauvetre, Raymond Tetrahedron, 1991 , vol. 47, # 37 p. 7767 - 7774

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Citation Number: 23

Abstract

A one-pot stereospecific synthesis of 1, 5-dien-3-ynes (Z) or (E) is described, based upon a palladium-catalyzed cross-coupling reaction between butenynylzinc bromide, generated in situ from 1, 1-difluoroethylene, and an adequate iodoalkene. These dienynes are converted into the corresponding trienic compounds by (Z) semi-hydrogenation.