Recent studies have shown that the conformational preferenceof the S-0 bond in six membered ring sulphoxdes varies somewhat unpredictably with the atom or group 1n the p-posltlon. Thus thiane l-oxide 1 exists predominantly as
Equatorial SO bond in 1,3-dithiane-1-oxides
✍ Scribed by M.J. Cook; A.P. Tonge
- Book ID
- 104246728
- Publisher
- Elsevier Science
- Year
- 1973
- Tongue
- French
- Weight
- 119 KB
- Volume
- 14
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
The axial preference shown by the S.0 bond of thiane-l-oxide is well established' and Harpp and Gleason2 showed recently that this preference is exhibited in 1,2-dithiane-l-oxide also. Current interest3 in the effect of heteroatom X on the orientation of R in rings of type 1 prompted us to examine some 1,3-dithiane-l-oxides, and we now report 4a that the "normal" axial preference of the sulphinyl oxygen is reversed in this ring system.
📜 SIMILAR VOLUMES
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