Acid-catalysed aromatisation of benzene cis-1,2-dihydrodiols: a carbocation transition state poorly stablised by resonance
- 1 January 1994
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Chemical Communications
- No. 3,p. 313-314
- https://doi.org/10.1039/c39940000313
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.Keywords
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