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

Reference:

Buchanan, J. G., Diggle, R. A., Ruggiero, G. D. and Williams, I. H., 2006. The Walden cycle revisited: a computational study of competitive ring closure to alpha- and beta-lactones. Chemical Communications

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Abstract

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

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