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
Full text available as: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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