The thermal isomerization of 1??(α??aroyloxybenzylideneamino)??4, 5??di??methyl??1, 2, 3??triazoles (isoimides) to the corresponding imides

AJ Maroulis…

Index: Maroulis, A. J.; Hadjiantoniou - Maroulis, C. P. Journal of Heterocyclic Chemistry, 1984 , vol. 21, p. 1653 - 1656

Full Text: HTML

Citation Number: 4

Abstract

Abstract The title isoimides rearrange upon heating to the corresponding imides through a [1, 3] O⇀ N aroyl transfer. The reaction is slightly accelarated by electron withdrawing substituents in the migrating moiety and retarded by electron donating as it is suggested by the positive (+ 0.5) Hammett ϱ value. The mechanism operating is either a rate determining nucleophilic attack by the nitrogen lone pair on the carbonyl carbon or a sigmatropic [π2s+ ...