Synthesis and Reactions of 1-Azirines

Alfred Hassner, Frank W. Fowler

Research output: Contribution to journalArticlepeer-review

179 Scopus citations

Abstract

A general synthesis of 1-azirines is described involving the photolysis of vinyl azides, which in turn can be readily obtained from the corresponding olefins. The photolysis usually proceeds in high yield and can also be applied to the synthesis of fused azirines. Infrared and nmr spectral properties as well as reactions of 1-azirines are discussed. Photolysis of vinyl azides in methanol containing sodium methoxide leads to amino ketals that provide a regiospecific synthesis of α-amino ketones. The ketals were shown to arise from the addition of methanol to the azirine followed by a ring opening of the 2-methoxyaziridine in methanol. Lithium aluminum hydride reduction of 1-azirines occurs in a stereospecific manner to give cis-2,3-disubstituted aziridines.

Original languageEnglish
Pages (from-to)2869-2875
Number of pages7
JournalJournal of the American Chemical Society
Volume90
Issue number11
DOIs
StatePublished - 1 May 1968
Externally publishedYes

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