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

doi:10.1039/b517461a

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

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

9 Citations (SciVal)

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 language	English
Pages (from-to)	1106-1108
Number of pages	3
Journal	Chemical Communications
Issue number	10
DOIs	https://doi.org/10.1039/b517461a
Publication status	Published - 2006

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ID number: ISI:000235992900016

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10.1039/b517461a

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

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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T1 - The Walden cycle revisited: a computational study of competitive ring closure to alpha- and beta-lactones

AU - Buchanan, J G

AU - Diggle, R A

AU - Ruggiero, G D

AU - Williams, I H

N1 - ID number: ISI:000235992900016

PY - 2006

Y1 - 2006

N2 - 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.

AB - 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.

U2 - 10.1039/b517461a

DO - 10.1039/b517461a

M3 - Article

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EP - 1108

JO - Chemical Communications

JF - Chemical Communications

IS - 10

ER -

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

Abstract

Bibliographical note

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