Acid-catalysed rearrangement of cyclic alcohols with neighbouring syn or anti phenylthio groups leads to allylic sulfides with endo- or exo-cyclic double bonds. Only the anti alcohols rearrange for ring sizes n= 5–10 but the syn alcohol rearranges if n= 12 or 15. The reasons for the product distribution, both regio- and stereo-chemical, are examined by molecular mechanics calculations.
M. Hannaby, P. Judson and S. Warren, J. Chem. Soc., Perkin Trans. 1, 1992, 2609 DOI: 10.1039/P19920002609
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