Tetrahedron Letters

Modification of the Fritsch–Buttenberg–Wiechell rearrangement: a facile route to unsymmetrical butadiynes

ET Chernick, S Eisler, RR Tykwinski

Index: Chernick, Erin T; Eisler, Sara; Tykwinski, Rik R Tetrahedron Letters, 2001 , vol. 42, # 49 p. 8575 - 8578

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Citation Number: 15

Abstract

A modification of the Fritsch–Buttenberg–Wiechell rearrangement has been used to form unsymmetrically substituted 1, 3-butadiynes from 1, 1-dibromo-olefin precursors. The reaction proceeds via lithium–halogen exchange, followed by migration of the aryl or alkynyl moiety to provide the butadiyne framework. The facile formation of the dibromo-olefins in three steps from commercially available aryl aldehydes or carboxylic acid chlorides makes ...