Chemistry Letters
Online ISSN : 1348-0715
Print ISSN : 0366-7022
ISSN-L : 0366-7022
Exalted Resonance Effect in the Aryl-Assisted Solvolyses of 2-Aryl-2-(trifluoromethyl)ethyl m-Nitrobenzenesulfonates
Mutsuo OkamuraKen HazamaMie OhtaKeiko KatoTakaaki HoraguchiAtsuyoshi Ohno
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1997 Volume 26 Issue 10 Pages 973-974

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Abstract

The substituent effects on solvolysis of 2-aryl-2-(trifluoromethyl)ethyl m-nitrobenzenesulfonates, in acetic acid and in 80% aqueous trifluoroethanol, were analyzed by Yukawa-Tsuno equation. The resonance demands (r = 0.77 in acetic acid) were larger than that of standard aryl-assisted solvolysis by 0.2. This enlargement should depend on a destabilization of aryl-assisted transition-state by an electron-withdrawing trifluoromethyl group.

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© 1997 The Chemical Society of Japan
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