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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 19, Number 12
BKCSDE 19(12)
December 20, 1998 

Nucleophilic substitution Reactions of 2-Chloro-2-Propen-1-yl Arenesulfonates with Anilines and N,N-Dimethylanilines in Acetonitrile
Hyuck Keun Oh, Eun-Mi Jeong, Ikchoon Lee
Kinetic studies are carried out on the reactions of 2-chloro-2-propen-1-yl arenesulfonates with anilines and N,N-dimethylanilines in acetonitrilile at 45.0 ℃. The 2-chloro substituent is found to deactive the allyl moiety with considerable decrease in the rates. The sign and magnitude of the cross-interaction constant (ρxz 0.3) and the inverse secondary kinetic isotope effect (kH/kD 0.92) support an SN2 mechanism with a relatively tight transition state. The possibility of an SN2' mechanism can be safely precluded based on the ρxz values observed.
1334 - 1336
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