The Journal of Organic Chemistry

Mechanism of base-promoted eliminative fragmentations of 2-alkyl-3-phenyloxaziridines

K Suda, F Hino, C Yijima

Index: Suda, Kohji; Hino, Fumio; Yijima, Chino Journal of Organic Chemistry, 1986 , vol. 51, # 22 p. 4232 - 4239

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Citation Number: 7

Abstract

The base-promoted fragmentations of 2-benzy1-3-(4-substituted-phenyl) oxaziridines 1 and 2-(4-substituted-benzyl)-3-phenyloxaziridines 2 in anhydrous organic solvents give benzaldehydes and unstable benzylideneimines. The subsequent trimerization of the imines provides the benzylidene animals with the liberation of ammonia. The fragmentations can be regarded as an a, p-elimination and have been studied kinetically with triethylamine in ...