Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Nucleophilic Substitution Reactions of Benzyl Benzenesulfonates with Benzylamine in Acetonitrile and Methanol

  • Published : 1991.06.20
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Abstract

Kinetic studies of the reactions of benzyl benzenesulfonates with benzylamines in methanol and acetonitrile have been carried out. The reaction was found to proceed by a dissociative $S_N2$ in MeCN but by an associative $S_N2$ mechanism in MeOH. The transition state was rather loose in MeCN whereas it was tight in MeOH, in contrast to a tighter TS in MeCN for the corresponding reactions with aniline. The reaction of benzylamine in MeOH was characteristic of the highly solvated nucleophile, benzylamine, compared to the normal reaction in MeCN.

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