Catalyst-product dependency in the transition metal catalyzed decomposition of ethyl 3-diazo-2-oxopropionate. An unusual Wolff rearrangement

S Bien, Y Segal

Index: Bien,S.; Segal,Y. Journal of Organic Chemistry, 1977 , vol. 42, p. 1685 - 1688

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Citation Number: 25

Abstract

Competitive cyclopropanation, allylic insertion, and Wolff rearrangement have been observed in the catalytic decomposition of ethyl 3-diazo-2-oxopropionate in the presence of cyclohexene. The course of the decomposition could be controlled by use of transition-metal catalysts: highly selective formation of the norcaryl derivative 2 or the malonate 4 could be achieved by appropriate choice of catalyst. The formation of 4 has been interpreted by the ...