Issue 5, 1983

Oxidative coupling of phenols. Part 8. A theoretical study of the coupling of phenoxyl radicals

Abstract

A theoretical study is described of the stereochemistry of mutual approach of two phenoxyl radicals. Both the CNDO and MINDO/3 methods are used and Morse curves are calculated for each reaction where the reaction co-ordinate is the interplanar distance. From a number of possible stereochemistries the most favoured involves an initial coaxial sandwich geometry, which undergoes conformational changes as bond formation between the two radical species occurs. The most energetically favoured path, which is given by the staggered form of the rings, leads to ortho-para- and ortho-ortho-coupled products. Of lesser importance is a head-to-tail approach which can lead to either ortho-ortho-carbon coupling or para-oxygen coupling. The para-para- and ortho-para-couplings obtained from the eclipsed form are of still smaller significance.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 2, 1983, 575-579

Oxidative coupling of phenols. Part 8. A theoretical study of the coupling of phenoxyl radicals

D. R. Armstrong, C. Cameron, D. C. Nonhebel and P. G. Perkins, J. Chem. Soc., Perkin Trans. 2, 1983, 575 DOI: 10.1039/P29830000575

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Spotlight

Advertisements