Issue 12, 2001
From the journal:

Journal of the Chemical Society, Perkin Transactions 2

Comparison of a protonated quinone methide and a methoxybenzyl carbocation analog

Robert A. McClelland,*a   Maeve M. Moriartya  and  Jacqueline M. Chevaliera  

* Corresponding authors

a Department of Chemistry, University of Toronto, Toronto, Ontario M5S 3H6, Canada

Abstract

The ratio of rate constants for the hydration of the bis(p-methoxyphenyl)methyl cation and the (p-hydroxyphenyl)(p-methoxyphenyl)methyl cation is 1.75 ∶ 1. Thus a methoxybenzyl carbocation is a good model for a protonated p-quinone methide, and the stabilizing effect of hydration on the OH compound is minimal.

Graphical abstract: Comparison of a protonated quinone methide and a methoxybenzyl carbocation analog

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Article information

DOI
https://doi.org/10.1039/B107687F
Article type
Communication
Submitted
24 Aug 2001
Accepted
16 Oct 2001
First published
02 Nov 2001

J. Chem. Soc., Perkin Trans. 2, 2001, 2235-2236

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Comparison of a protonated quinone methide and a methoxybenzyl carbocation analog

R. A. McClelland, M. M. Moriarty and J. M. Chevalier, J. Chem. Soc., Perkin Trans. 2, 2001, 2235 DOI: 10.1039/B107687F

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