Attempted generation of azacyclopropenones a new route to nitriles

A. Hassner, R. J. Isbister, R. B. Greenwald, J. T. Klug, E. C. Taylor

Research output: Contribution to journalArticlepeer-review

27 Scopus citations


A synthesis of the unknown azacyclopropenone (azirinone) system was attempted via α-azido ketenes. Treatment of α-azido acid chlorides with triethylamine, in an attempt to generate α-azido ketenes, led in good yield to nitriles containing one less carbon. At -60° it was possible to trap the α-azido ketene 7c with benzalaniline to form a β-lactam. The formation of nitriles most likely proceeds by intermediacy of an azirinone. The sequence of reactions provides a useful degradation of carboxylic acids to nitriles with loss of one carbon.

Original languageEnglish
Pages (from-to)1637-1641
Number of pages5
Issue number8
StatePublished - 1969
Externally publishedYes


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