Enediynes from Aza-Enediynes: C,N-Dialkynyl Imines Undergo Both Aza-Bergman Rearrangement and Conversion to Enediynes and Fumaronitriles

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Abstract

[reaction; see text] Aza-enediynes (C,N-dialkynyl imines) undergo thermal aza-Bergman rearrangement to beta-alkynyl acrylonitriles through 2,5-didehydropyridine (2,5-ddp) intermediates. Certain aza-enediynes also undergo an alternative process affording enediynes and fumaronitriles. Studies employing a specifically (l3)C-labeled aza-enediyne show that the conversion to enediyne is second order in aza-enediyne, proceeds by a "head-to-tail" coupling, and affords the (Z)-enediyne.

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