Schwefelwasserstoff reagiert mit den 16fl,17@Epoxyketonen 41, c-e zu den trans-Mercaptohydrinen 5% c-e, die mit Aceton bzw. Acetophenon die 1,3-Oxathiolane 7% c-e bzw. 8d bilden. Als SpthesiS Of 17-ThiOpWgllMeSHydrogen sulfide reacts with the 16fl,17~poxyketones 4% c-e to give the trans-mercaptohydrins 5% c-e, which, when treated with acetone or acetophenone, yield the 1,3-oxathiolanes 7% c-e, and 8d, respectively. In addition to 74 there was also isolated the 16fl,17@thioacetonide 10. By oxidation of 7d there was obtained the sulfone 9. Acetylation of Sd yielded the I7a-thioacetate 13 and a second product which is probably the 17p-cpimer 14. Treatment of Se with methanesulfonyl chloride at 0°C resulted in the formation of the bissteroid 15 whereas at 60°C there was isolated the episulfide 16 in addition to IS. Thiocyanic acid was capable of opening the 16fl,17@ epoxide 4d to form the isomeric thiocyanates 18 and 19 as well as the thiocarbonate 20.
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