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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 12, Number 3
BKCSDE 12(3)
March 20, 1991

Title	Nucleophilic Substitution Reactions of Benzyl Benzenesulfonates with Benzylamine in Acetonitrile and Methanol
Author	Ikchoon Lee*, Chul Hyun Kang, Pyoung Sam Park, Hai Whang Lee
Keywords
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 SN2 in MeCN but by an associative SN2 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.
Page	282 - 286
Full Text	PDF

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