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Issue 3, 1994
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Acid-catalysed aromatisation of benzene cis-1,2-dihydrodiols: a carbocation transition state poorly stablised by resonance

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.

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Article type: Paper
DOI: 10.1039/C39940000313
Citation: J. Chem. Soc., Chem. Commun., 1994,0, 313-314
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    Acid-catalysed aromatisation of benzene cis-1,2-dihydrodiols: a carbocation transition state poorly stablised by resonance

    D. R. Boyd, J. Blacker, B. Byrne, H. Dalton, M. V. Hand, S. C. Kelly, R. A. M. O'ferrall, S. N. Rao, N. D. Sharma and G. N. Sheldrake, J. Chem. Soc., Chem. Commun., 1994, 0, 313
    DOI: 10.1039/C39940000313

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