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 language | English (US) |
|---|---|
| Pages (from-to) | 237-241 |
| Number of pages | 5 |
| Journal | Journal of the Chemical Society, Perkin Transactions 2 |
| Issue number | 2 |
| State | Published - 1987 |
| Externally published | Yes |
ASJC Scopus subject areas
- Chemistry(all)
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Lebrilla, C. B., & Schwarz, H. (1987). An MNDO study of the unimolecular reactions of methyl acetate and its sulphur analogues. Journal of the Chemical Society, Perkin Transactions 2, (2), 237-241.