F. Fowler
1971
Citations
0
Influential Citations
40
Citations
Journal
Advances in Heterocyclic Chemistry
Abstract
Publisher Summary Azirine is the term used to describe a three-membered heterocycle containing one nitrogen atom and one double bond. There are two isomeric azirines (1 and 2), which have been designated by Chemical Abstracts and “The Ring Index,” as 1H- and 2H-azirine, respectively. The 2-azirine ring system is of theoretical interest since it is a cyclic conjugated structure containing 477 electrons and is predicted by Huckel's rule not to be stabilized by cyclic delocalization. Electronically it is analogous to cyclobutadiene. The chapter discusses about synthesis of 1-azirines and neber reaction and related reactions, the preparation and decomposition of vinyl azides, photolysis and pyrolysis of isoxazoles, and some miscellaneous 1 -azirine synthesis. Reactions of 1-azirines in case of electrophilic reagents, nucleophilic reagents, and cycloadditions are also studied. It is clear from this review that our knowledge of the azirine ring system is still in its infancy. Although a considerable number of 1-azirines have been prepared in a very short time, discovery of new and refinement of old synthetic techniques are clearly needed. Finally, the 1-azirine ring system is potentially a very valuable starting point for the preparation of new and unusual heterocyclic compounds. Already a number of very interesting aziridines have been prepared and 1 -azirines were key intermediates for the preparation of the 1 -azabicyclo[2.1 .0]pentane and 1-azabicyclo[l.l .0]butane ring systems.