Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Nucleophilic Substitution Reactions of 2-Chloro-2-Propen-1-yl Arenesulfonates with Anilines and N,N-Dimethylanilines in Acetonitrile

  • Published : 1998.12.20
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Abstract

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.

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