Aminolysis of Y-Substituted Phenyl Diphenylphosphinates and Benzoates: Effect of Modification of Electrophilic Center from CO to PO

IH Um, YH Shin, JY Han, M Mishima

Index: Um, Ik-Hwan; Shin, Young-Hee; Han, Jeong-Yoon; Mishima, Masaaki Journal of Organic Chemistry, 2006 , vol. 71, # 20 p. 7715 - 7720

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Citation Number: 83

Abstract

The effect of modification of the electrophilic center from CO to PO on reactivity and reaction mechanism has been investigated for aminolysis of Y-substituted phenyl diphenylphosphinates (1a-j) and benzoates (2a-i). The phosphinates 1a-j are less reactive than the benzoates 2a-i. The reactions of 2, 4-dinitrophenyl diphenylphosphinate (1a) with alicyclic secondary amines resulted in a linear Brønsted-type plot with a βnuc value of ...