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Acid-catalyzed aromatization of benzene CIS-1,2-dihydrodiols - a carbocation transition-state poorly stabilized by resonance

Boyd, DR, Blacker, J, Byrne, B, Dalton, H, Hand, MV, Kelly, SC, Oferrall, RAM, Rao, SN, Sharma, ND and Sheldrake, GN (1994) 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). 313 - 314 . ISSN 0022-4936

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Abstract

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

Item Type: Article
Keywords: monocyclic arenes, dihydrodiols, phenanthrene, excess
Academic Units: The University of Leeds > Faculty of Maths and Physical Sciences (Leeds) > School of Chemistry (Leeds)
Depositing User: Symplectic Publications
Date Deposited: 11 Apr 2012 12:20
Last Modified: 08 Feb 2013 17:37
Published Version: http://dx.doi.org/10.1039/C39940000313
Status: Published
Publisher: Royal Society of Chemistry
Identification Number: 10.1039/C39940000313
URI: http://eprints.whiterose.ac.uk/id/eprint/43835

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