Issue 10, 2006

The Walden cycle revisited: a computational study of competitive ring closure to α- and β-lactones

Abstract

The text-book Walden cycle which interconverts the stereochemical configurations of chlorosuccinic and malic acids involves a β-lactone intermediate in preference to an α-lactone intermediate because the Onuc C Cl angle in the transition structure for the former (174°) is more favourable than that for the latter (139°), as determined by PCM(ε = 78.4)/B3LYP/6-31+G* calculations; the smaller ring-strain energy of the β-lactone contributes little to the reactivity difference.

Graphical abstract: The Walden cycle revisited: a computational study of competitive ring closure to α- and β-lactones

Article information

Article type
Communication
Submitted
12 Dec 2005
Accepted
18 Jan 2006
First published
01 Feb 2006

Chem. Commun., 2006, 1106-1108

The Walden cycle revisited: a computational study of competitive ring closure to α- and β-lactones

J. G. Buchanan, R. A. Diggle, G. D. Ruggiero and I. H. Williams, Chem. Commun., 2006, 1106 DOI: 10.1039/B517461A

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