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CuCl-Induced Formation and Migration of Isoindazolyl Carbenoids

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posted on 30.03.2007, 00:00 by Laura D. Shirtcliff, Michael M. Haley, Rainer Herges
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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