CuCl-induced formation and migration of isoindazolyl carbenoids

LD Shirtcliff, MM Haley, R Herges

Index: Shirtcliff, Laura D.; Weakley, Timothy J. R.; Haley, Michael M.; Koehler, Felix; Herges, Rainer Journal of Organic Chemistry, 2004 , vol. 69, # 21 p. 6979 - 6985

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Citation Number: 24

Abstract

Two azo-ene-butadiyne conjugated systems undergo CuCl-mediated cyclization to afford isoindazolyl carbenoids that could be trapped with 2, 3-dimethyl-2-butene as [2+ 1] cycloaddition products. X-ray structure analysis of the resultant cyclopropanes showed that formal migration to the distal carbenoid isomer and subsequent trapping had occurred. The possible CuCl-induced cyclization/migration pathways were explored using density ...