Rearrangement of alkynyl and vinyl carbenoids via the rhodium (II)-catalyzed cyclization reaction of. alpha.-diazo ketones

…, DJ Austin, Y Gareau, JM Kassir, SL Xu

Index: Padwa, Albert; Austin, David J.; Gareau, Yves; Kassir, Jamal M.; Xu, Simon L. Journal of the American Chemical Society, 1993 , vol. 115, # 7 p. 2637 - 2647

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Citation Number: 75

Abstract

Abstract: 0-Alkynyl-substituted a-diazoacetophenones undergo facile cyclization to indenone derivatives upon treatment with catalytic quantities of Rh (I1) carboxylates. The cyclization reaction involves addition of a rhodium stabilized a-keto carbenoid onto the neighboring acetylenic n-bond to give a cyclized vinyl carbenoid. When an alkene is tethered to the alkynyl group, the vinyl carbenoid complex undergoes further cyclization to ...