Effect of amine nature on reaction rate and mechanism in nucleophilic substitution reactions of 2, 4-dinitrophenyl X-substituted benzenesulfonates with alicyclic …

…, SM Chun, OM Chae, M Fujio, Y Tsuno

Index: Um, Ik-Hwan; Chun, Sun-Mee; Chae, Ok-Mi; Fujio, Mizue; Tsuno, Yuho Journal of Organic Chemistry, 2004 , vol. 69, # 9 p. 3166 - 3172

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Citation Number: 78

Abstract

Second-order rate constants have been measured for reactions of 2, 4-dinitrophenyl X- substituted benzenesulfonates with a series of alicyclic secondary amines. The reaction proceeds through SO and CO bond fission pathways competitively. The SO bond fission occurs more dominantly as the amine basicity increases and the substituent X in the sulfonyl moiety becomes more strongly electron withdrawing, indicating that the regioselectivity is ...