Issue 8, 2002
From the journal:

Journal of the Chemical Society, Perkin Transactions 2

Diels–Alder reactions of 1,1,3-triarylallyl cations: determination of the free energy of concert†‡

Claudia Fichtner§a  and  Herbert Mayr*a  

* Corresponding authors

a Department Chemie, Ludwig-Maximilians-Universität München, Butenandtstr. 5–13 (Haus F), D-81377 München, Germany
E-mail: Herbert.Mayr@cup.uni-muenchen.de
Fax: int. +49 (0) 89-2180 7717

Abstract

1,1,3-Triarylallyl cations react with 1,3-dienes to give Diels–Alder products in low to moderate yields. The observed second-order rate constants agree with those calculated for the stepwise processes by the correlation log k(20 °C) = s(N + E) [eqn. (1)] indicating the absence of a significant free energy of concert. Eqn. (1) can, therefore, also be employed for the prediction of absolute rate constants of Diels–Alder reactions of allyl cations.

Graphical abstract: Diels–Alder reactions of 1,1,3-triarylallyl cations: determination of the free energy of concert

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Article information

DOI
https://doi.org/10.1039/B203555C
Article type
Paper
Submitted
11 Apr 2002
Accepted
13 May 2002
First published
28 Jun 2002

J. Chem. Soc., Perkin Trans. 2, 2002, 1441-1444

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Diels–Alder reactions of 1,1,3-triarylallyl cations: determination of the free energy of concert

C. Fichtner and H. Mayr, J. Chem. Soc., Perkin Trans. 2, 2002, 1441 DOI: 10.1039/B203555C

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