EXALTED RESONANCE EFFECT IN THE ARYL-ASSISTED SOLVOLYSES OF 2-ARYL-2-(TRIFLUOROMETHYL)ETHYL M-NITROBENZENESULFONATES

Authors
OKAMURA M HAZAMA K OHRA M KATO K HORAGUCHI T OHNO A
Citation
M. Okamura et al., EXALTED RESONANCE EFFECT IN THE ARYL-ASSISTED SOLVOLYSES OF 2-ARYL-2-(TRIFLUOROMETHYL)ETHYL M-NITROBENZENESULFONATES, Chemistry Letters, (10), 1997, pp. 973-974
Citations number
22
Categorie Soggetti
Chemistry
Journal title
Chemistry Letters → ACNP
ISSN journal
03667022
Issue
10
Year of publication
1997
Pages
973 - 974
Database
ISI
SICI code
0366-7022(1997):10<973:EREITA>2.0.ZU;2-F
Abstract
The substituent effects on solvolysis of 2-aryl-2-(trifluoromethyl)eth yl m-nitrobenzenesulfonates, in acetic acid and in 80% aqueous trifluo roethanol, were analyzed by Yukawa-Tsuno equation. The resonance deman ds (r = 0.77 in acetic acid) were larger than that of standard aryl-as sisted solvolysis by 0.2. This enlargement should depend on a destabil ization of aryl-assisted transition-state by an electron-withdrawing t rifluoromethyl group.