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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 17, Number 3
BKCSDE 17(3)
March 20, 1996 

Nucleophilic Substitution Reactions of 1- and 2-Naphthylethyl Arenesulfonates with Anilines and Benzylamines
Hyuck Keun Oh, Se Jeong Song, In Ho Cho, Ikchoon Lee*
Nucleophilic substitution reactions of 1- and 2-naphthylethyl arenesulfonates, 2 and 3, with anilines and benzylamines in methanol at 65.0 ℃ are investigated. The rates are slower than those for the corresponding derivatives of 2-phenylethyl arenesulfonates, 1, which can be attributed to a greater degree of positive charge stabilization at Cα in the transition state (TS) by a greater electron supply from a phenyl ring compared to a naphthyl ring. The mechanism for the two naphthylethyl systems are similar to that for the 2-phenylethyl derivatives, except that the transition state is formed at somewhat an earlier position along the reaction coordinate. The secondary kinetic isotope effects involving deuterated nucleophilies indicate that naphthylethyl series are sterically more crowded in the TS than 2-phenylethyl system. The data in this work can not elucidate the possible participation of the aryl-assisted pathway in the reaction.
254 - 257
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