Steroidal sulphur compounds. Part XII. Regiospecific formation of steroidal olefins by thermolysis of sulphoxides

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Abstract
The first examples of the regiospecific generation of isomeric olefins from two sulphoxides diastereoisomeric at sulphur are reported. Thermolysis of (R)- and (S)-3α-(1-adamantylsulphinyl)-5α-cholestane at 110 °C gave respectively 5α-cholest-3-ene and 5α-cholest-2-ene; (S)-3β-(1-adamantylsulphinyl)-5β-cholestane gave 5β-cholest-3-ene at a rate much greater than that at which the diastereoisomeric (R)-sulphoxide decomposed to 5β-cholest-2-ene, so providing a convenient preparation of these erstwhile rather inaccessible olefins. In contrast, thermolysis of 3α-(1-naphthyl)- and 3α-(anthracen-9-yl)-5α-cholestanes was not highly regioselective, and the corresponding steroidal diphenyl sulphoxides underwent stereomutation at sulphur more readily than elimination to give olefins.

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