The Cycloaddition of Vinyl Azides to Ketenes

Alfred Hassner, A. S. Miller, M. J. Haddadin

Research output: Contribution to journalArticlepeer-review

17 Scopus citations

Abstract

Vinyl azides undergo slow cycloaddition with diphenylketene (2) leading to five-membered ring enamino ketones 6 with loss of N2. The reaction appears to involve nucleophilic attack of the β carbon from the vinyl azide upon the ketene. A substantial improvement in yield of 6 is achieved by generating 2 in situ from a diazo ketone in solution. Treatment of the enamino ketones with phosphorus pentachloride or chlorine leads to a chlorination. In the case of 2-azido-1-hexene, cycloaddition with 2 proceeds with formation of cyclobutanones.

Original languageEnglish
Pages (from-to)2682-2685
Number of pages4
JournalJournal of Organic Chemistry
Volume37
Issue number17
DOIs
StatePublished - 1 Aug 1972
Externally publishedYes

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