Et. Chernick et al., Modification of the Fritsch-Buttenberg-Wiechell rearrangement: a facile route to unsymmetrical butadiynes, TETRAHEDR L, 42(49), 2001, pp. 8575-8578
A modification of the Fritsch-Buttenberg-Wiechell rearrangement has been us
ed to form unsymmetrically substituted 1,3-butadiynes from 1,1-dibromo-olef
in precursors. The reaction proceeds via lithium-halogen exchange, followed
by migration of the aryl or alkynyl moiety to provide the butadiyne framew
ork. The facile formation of the dibromo-olefins in three steps from commer
cially available aryl aldehydes or carboxylic acid chlorides makes this pro
cedure an attractive alternative to traditional methods for butadiyne synth
esis. (C) 2001 Elsevier Science Ltd. All rights reserved.