Vinylic organoboranes. 13. A convenient stereospecific synthesis of (Z)-1-halo-1-alkenes from 1-alkynes via (E)-1-alkenylborane derivatives with halogens

HC Brown, C Subrahmanyam, T Hamaoka…

Index: Brown, Herbert C.; Subrahmanyam, Chitti; Hamaoka, Tsutomu; Ravindran, Nair; Bowman, Donald H.; et al. Journal of Organic Chemistry, 1989 , vol. 54, # 26 p. 6068 - 6075

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Citation Number: 63

Abstract

The reaction of (E)-1-alkenylborane derivatives with bromine under various conditions was investigated, and a simple stereospecific synthesis of (2)-1-bromo-1-alkenes has been developed. Addition of bromine to (E)-1-alkenyldisiamylborane, derived from the reaction of 1-alkynes with bis (3-methyl-2-buty1) borane (Sia2BH), gives either (2)-or (E)-1-bromo-1- alkenes, depending upon the procedure used to eliminate the elements of disiamylboron ...