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A remarkable difference in the conformational preference of the so-bond in 1,3-di-thiane-1-oxides and 1,3-oxathiane-3-oxides.

โœ Scribed by L. Van Acker; M. Anteunis

Publisher
Elsevier Science
Year
1974
Tongue
French
Weight
196 KB
Volume
15
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

The sulfoxide group shows a lot of interesting stereochemical features (2).

In thiane-l-oxide the axial conformation (62% of the mixture at -9OOC) is favored by 175 Cal/mole (2). Introduction of a 3,3-dimethyl grouping reverses this axial

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The title compounds (2 and 4) obtained by the diastereoselective hydrogenation of the corresponding 1,2,3,6-tetrahydrophosphinine oxides (1 and 3) were subjected to a detailed quantum chemical study. The possible chair conformers were calculated at the HF/6-31G \* level of theory, according to which

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Conformational ;f;ects in 1,3-dioxans and 1,3-dithianes have been recently largely elucidated. -That is why we started a systematic study of alkyl-substituted 1,3-oxathianes to compare their conformational features with those of their above-mentioned symmetric analogs. GELAN and ANTEURIS investigat