Tetrahedron

Reactions with aziridines-39: Ring opening of activated 2, 2-dimethylaziridines by grignard reagents. A mechanistic study

A Onistschenko, B Buchholz, H Stamm

Index: Onistschenko, Andreas; Buchholz, Berthold; Stamm, Helmut Tetrahedron, 1987 , vol. 43, # 3 p. 565 - 576

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Citation Number: 14

Abstract

Reaction of activated 2, 2-dimethylaziridines 1 with Grignard reagents RMgHal in boiling THF can yield the products 2 of normal aziridine ring opening, the rearranged opening products 3, and the methallylamides 4 (isomers of 1). The product distribution depends on R, Hal, and experimental conditions, and very strongly on the nature of the activating group A. It is shown that 1 is opened (reversibly for A= sulfonyl) forming 10 through a Lewis acid ...

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