Skeletal reorganization of enynes catalyzed by InCl3.

Y. Miyanohana,N. Chatani

Published 2006 in Organic Letters

ABSTRACT

[reaction: see text] The skeletal reorganization of enynes is achieved by the presence of InCl(3) as the catalyst. The reaction of enynes having a terminal acetylenic moiety proceeds in a stereospecific manner to give 1-vinylcycloalkenes. The reaction of enynes containing an alkyl group on the acetylenic terminal carbon resulted in a new type of skeletal reorganization to give 1-allylcycloalkenes, formation of which involves a double cleavage of the C-C double bond and the triple bond.

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