Journal of Organic Chemistry

Mechanism of the isomerization of 1-(arylthiocarbonyl) aziridines to 2-(arylthioalkyl) isocyanates

DA Tomalia, DP Sheetz, GE Ham

Index: Tomalia,D.A. et al. Journal of Organic Chemistry, 1970 , vol. 35, # 1 p. 47 - 52

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Citation Number: 5

Abstract

It has been shown that the isomerization of 1-(arylthiocarbony1) aziridines to 2-(arylthioalkyl) isocyanates is catalyzed by triethylamine or thiophenolate ion and may occur under relatively mild conditions (25-77'). 1-(Arylthiocarbonyl)-2-methylaziridines rearranged to their isomeric isocyanates by selective ring fission at the unsubstituted aziridine ring carbon, thus indicating the SN2 character of these rearrangements. Kinetic experiments have shown ...