Tetrahedron Letters

Nucleophilic cleavage of 2, 2-dimethylaziridines: competition between SN2 and postulated “SET” mechanism.

H Stamm, P Assithianakis, B Buchholz, R Weiβ

Index: Stamm, H.; Assithianakis, P.; Buchholz, B.; Weiss, R. Tetrahedron Letters, 1982 , vol. 23, # 48 p. 5021 - 5024

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Citation Number: 41

Abstract

Abstract Regioselectivity of nucleophilic attack on 2, 2-dimethylaziridines depends on the degree of leaving group activation: in highly activated aziridines it occurs at the methylene carbon and in less activated at the tertiary carbon. This latter abnormal ring opening is explained by an SET mechanism.

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