Isolation of a cyclopropane-containing product from the rearrangement of a 3-aza-3-ene-1,5-diyne under acid catalysis |
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| Authors: | Liping FengSean M. Kerwin |
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| Affiliation: | Division of Medicinal Chemistry, College of Pharmacy, Institute for Cellular and Molecular Biology, University of Texas at Austin, Austin, TX 78712, USA |
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| Abstract: | A 3-aza-enediyne that undergoes rapid aza-Bergman rearrangement was treated with trifluoromethanesulfonic acid in the presence of 1,4-cyclohexadiene in an attempt to trap the putative 2,5-didehydropyridinium aza-Bergman intermediate. No pyridine products were detected; rather, a cyclopropane derivative of 1,4-cyclohexadiene derived from a 5-oxazolylcarbene was isolated. |
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