Kinetics and Mechanism of the Aminolysis of Cycloalkylmethyl Arenesulfonates

HK Oh, SJ Song, DS Jo, I Lee

Index: Oh, Hyuck Keun; Song, Se Jeong; Jo, Dong-Soo; Lee, Ikchoon Journal of Physical Organic Chemistry, 1997 , vol. 10, # 2 p. 91 - 96

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Citation Number: 4

Abstract

Abstract Nucleophilic substitution reactions of cycloalkylmethyl arenesulfonates (C m H 2n− 1 CH 2 OSO 2 C 6 H 4 Z) with anilines (XC 6 H 4 NH 2) in methanol at 65.0 C were studied. The reactivity order (n= 4> 6> 7> 5) reflects largely the order of steric effect of the ring size (SEs term) except for n= 5, which exhibits the least reactivity. This reversal of the order for n= 5 is considered to result from large rate retardation due to polar effect of the ρ* σ* term. ...