An MNDO study of the unimolecular reactions of methyl acetate and its sulphur analogues

Carlito B Lebrilla, Helmut Schwarz

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6 Citations (Scopus)

Abstract

The unimolecular reactions of methyl acetate and its sulphur analogues, S-methyl and O-methyl monothioacetate and methyl dithioacetate, were investigated using the semi-empirical MNDO method with respect to ketene-thioketene formation and 1,3-methyl migration. For methyl acetate, 1,3-methyl migration of the methyl ester was calculated to be more favourable than ketene formation. S-Methyl monothioacetate undergoes ketene formation preferentially while O-methyl monothioacetate rearranges via 1,3-methyl migration to the more thermodynamically stable S-methyl isomer. Methyl dithioacetate also prefers methyl migration; however, unlike the other three compounds, the theoretical results condtradict earlier reported experimental results.

Original languageEnglish (US)
Pages (from-to)237-241
Number of pages5
JournalJournal of the Chemical Society, Perkin Transactions 2
Issue number2
StatePublished - 1987
Externally publishedYes

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Sulfur
Isomers
Esters
methyl acetate
ketene

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

An MNDO study of the unimolecular reactions of methyl acetate and its sulphur analogues. / Lebrilla, Carlito B; Schwarz, Helmut.

In: Journal of the Chemical Society, Perkin Transactions 2, No. 2, 1987, p. 237-241.

Research output: Contribution to journalArticle

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