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

Carlito B Lebrilla, Helmut Schwarz

Research output: Contribution to journalArticle

6 Scopus citations

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

ASJC Scopus subject areas

  • Chemistry(all)

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