Preparation of the laevorotatory trans-(4S,6S)-4,6-dimethyl-1,3-dithiane and trans-(4S,6S)-4,6-dimethyl-1,3-oxathiane. An internal displacement of a secondary sulphonate leading to a cyclic thioacetal |
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| Authors: | D Danneels M Anteunis L van Acker D Tavernier |
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| Institution: | Department of Organic Chemistry, Laboratory for NMR Spectroscopy, State University at Ghent, Krijgslaan, 271, S.4bis, B-9000 Gent, Belgium |
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| Abstract: | (—)(2R,4R)-2,4-dimesyloxypentane, treated with (i) potassium thiolacetate/DMF (ii) 12N hydrogen chloride/dimethoxymethane/methanol yields (—)(4S,6S)-4,6-dimethyl-1,3-oxathiane and (—)(4S,6S)-4,6-dimethyl-1,3-dithiane. The mechanism of the formation of the oxathiane is discussed. |
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