Rhodium carbenoid mediated cyclizations of o-alkynyl-substituted. alpha.-diazoacetophenones

A Padwa, KE Krumpe, JM Kassir

Index: Padwa, Albert; Krumpe, Keith E.; Kassir, Jamal M. Journal of Organic Chemistry, 1992 , vol. 57, # 18 p. 4940 - 4948

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Citation Number: 55

Abstract

o-Akynyl-substituted a-diazoacetophenones undergo facile cyclization to indenone derivatives upon treatment with catalytic quantities of Rh (I1) carboxylates. A variety of structural influences were encountered by varying the nature of the substituent group attached to the alkyne carbon atom. The cyclization reaction involves addition of a rhodium stabilized carbenoid onto the acetylenic? r-bond to generate a vinyl carbenoid. The vinyl ...