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

J G Buchanan, R A Diggle, G D Ruggiero, I H Williams

Research output: Contribution to journalArticlepeer-review

8 Citations (Scopus)

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.
Original languageEnglish
Pages (from-to)1106-1108
Number of pages3
JournalChemical Communications
Issue number10
DOIs
Publication statusPublished - 2006

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