ACID-CATALYZED AROMATIZATION OF BENZENE CIS-1,2-DIHYDRODIOLS - A CARBOCATION TRANSITION-STATE POORLY STABILIZED BY RESONANCE

Authors
BOYD DR BLACKER J BYRNE B DALTON H HAND MV KELLY SC OFERRALL RAM RAO SN SHARMA ND SHELDRAKE GN
Citation
Dr. Boyd et al., ACID-CATALYZED AROMATIZATION OF BENZENE CIS-1,2-DIHYDRODIOLS - A CARBOCATION TRANSITION-STATE POORLY STABILIZED BY RESONANCE, Journal of the Chemical Society, Chemical Communications, (3), 1994, pp. 313-314
Citations number
18
Categorie Soggetti
Chemistry
Journal title
Journal of the Chemical Society, Chemical Communications → ACNP
ISSN journal
00224936
Issue
3
Year of publication
1994
Pages
313 - 314
Database
ISI
SICI code
0022-4936(1994):3<313:AAOBC->2.0.ZU;2-2
Abstract
Acid-catalysed dehydration of 3-substituted benzene cis-1,2-dihydrodio ls exhibits a Hammett plot with p = -8.2, consistent with reaction via a benzenonium ion-like intermediate; however, correlation of +M reson ance substituents suchas Me and MeO by sigma(p) rather than sigma(+) c onstants indicates a marked imbalance between resonance and inductive stabilisation of the transition state.