Tetrahedron

Mechanistic studies of amination of ketenimines: change of rate-determining step by N-substituents through electronic effects

K Sung, FL Chen, PM Huang, SM Chiang

Index: Sung, Kuangsen; Chen, Fu-Lin; Huang, Pin-Mei; Chiang, Shu-Min Tetrahedron, 2006 , vol. 62, # 1 p. 171 - 181

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Citation Number: 4

Abstract

Vinylidenediamine intermediate was not found in amination reactions of Ni-propyl-p- substituted-phenylketenimines with n-BuNH2, but it was found in amination reactions of Np- substituted-phenylphenylketenimines with n-BuNH2 by low-temperature 1H NMR spectrometer, indicating that the rate-determining step is changed from the first step (CN addition) to the second step (tautomerization) when N-substituent of the ketenimines is ...