Journal of the Chemical Society. Perkin transactions I p. 589 - 595 (1989)
Update date:2022-08-04
Topics:
Blake, Alexander J.
McNab, Hamish
Murray, M. Elizabeth-Ann
Flash vacuum pyrolysis of the dimethylamino-azapropenones (7)-(9) and -azapropenethione (12) gives nitriles and amides (or thioamide) in yields of ca. 30percent by an electrocyclisation-ring cleavage mechanism.This is a minor pathway for the triarylazapropenones (14) and (15) for which homolytic cleavage of the C-N bond gives rise to the major products.The X-ray crystal structures of (10) and (12) show that the conjugated systems are almost planar in the s-Z conformation, as required for the electrocyclic ring closure.
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