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

被引：46

作者：

BOYD, DR

BLACKER, J

BYRNE, B

DALTON, H

HAND, MV

KELLY, SC

OFERRALL, RAM

RAO, SN

SHARMA, ND

SHELDRAKE, GN

机构：

[1] ZENECA FINE CHEM & MFG ORG,DEPT PROC TECHNOL,HUDDERSFIELD HD2 1FF,W YORKSHIRE,ENGLAND

[2] UNIV WARWICK,DEPT BIOL SCI,COVENTRY CV4 7AL,W MIDLANDS,ENGLAND

[3] UNIV COLL DUBLIN,DEPT CHEM,DUBLIN 4,IRELAND

来源：

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS | 1994年 / 03期

关键词：

D O I：

10.1039/c39940000313

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Acid-catalysed dehydration of 3-substituted benzene cis-1,2-dihydrodiols exhibits a Hammett plot with p = -8.2, consistent with reaction via a benzenonium ion-like intermediate; however, correlation of +M resonance substituents suchas Me and MeO by sigma(p) rather than sigma(+) constants indicates a marked imbalance between resonance and inductive stabilisation of the transition state.

引用

页码：313 / 314

页数：2

共 18 条

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