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Updated: Jul 16, 2026

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
Published on: April 19, 2019
CuCl-induced formation and migration of isoindazolyl carbenoids
Laura D Shirtcliff1, Michael M Haley, Rainer Herges
1Department of Chemistry, University of Oregon, Eugene, Oregon 97403-1253, USA.
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 functional theory, which indicated that the reaction most likely occurred via coordination of CuCl to the distal alkyne bond.
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