Issue 3, 1987
From the journal:

Journal of the Chemical Society, Perkin Transactions 2

MINDO/3 study of the isomerization of 1-methylcyclohexylium ion to 1-ethylcyclopentylium ion. An alternative mechanism for this branching rearrangement

Pedro M. Viruela-Martín,   Ignacio Nebot-Gil,   Rafael Viruela-Martín  and  Josep Planelles  

Abstract

A MINDO/3 study of the rearrangement mechanism of 1-methylcyclohexylium ion to 1-ethylcyclopentylium ion is presented. The structures at three intermediates and three transition states have been calculated and characterized. The results show that a ring-contraction mechanism via a corner-protonated cyclopropane intermediate is a more adequate description of this process than one based on an H-bridged edge-protonated cyclopropane intermediate. The value calculated for the barrier height for the ring-expansion process (14.5 kcal mol–1) is in good agreement with the experimental value (15.4 kcal mol–1) for the activation energy. The proposed mechanism resembles the Wagner–Meerwein ring-contraction reaction.

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Article information

DOI
https://doi.org/10.1039/P29870000307
Article type
Paper

J. Chem. Soc., Perkin Trans. 2, 1987, 307-311

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MINDO/3 study of the isomerization of 1-methylcyclohexylium ion to 1-ethylcyclopentylium ion. An alternative mechanism for this branching rearrangement

P. M. Viruela-Martín, I. Nebot-Gil, R. Viruela-Martín and J. Planelles, J. Chem. Soc., Perkin Trans. 2, 1987, 307 DOI: 10.1039/P29870000307

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