Mechanism of thermal Z/E isomerization of substituted N-benzylideneanilines. Nature of the activated complex with an sp-hybridized nitrogen atom

…, H Furuta, HJ Hofmann, R Cimiraglia…

Index: Asano, Tsutomu; Furuta, Hiroyuki; Hofmann, Hans-Joerg; Cimiraglia, Renzo; Tsuno, Yuho; Fujio, Mizue Journal of Organic Chemistry, 1993 , vol. 58, # 16 p. 4418 - 4423

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Citation Number: 42

Abstract

In order to study the mechanism of thermal geometrical isomerization involving a sp2- hybridized nitrogen atom, kinetic effects of substituent, solvent, and pressure were studied in substituted N-benzylideneanilines. The effect of the substituent on the aniline moiety was almost independent of the electronic nature of the benzylidene group, and the results could be described satisfactorily by log (kllz,)= p [S+ r+(a+-ao)+ r (r-uO)], except for the 4-( ...