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Isolation of a cyclopropane-containing product from the rearrangement of a 3-aza-3-ene-1,5-diyne under acid catalysis

✍ Scribed by Liping Feng; Sean M. Kerwin

Book ID: 104253464
Publisher: Elsevier Science
Year: 2003
Tongue: French
Weight: 140 KB
Volume: 44
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(03)00675-0

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✦ Synopsis

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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