Add time:07/20/2019         Source:sciencedirect.com

A number of metal trifluoroacetates were reacted with the olefin 3β-acetoxyandrost-5-en-17-one (6). Palladium(II) trifluoroacetate afforded bis[μ-trifluoroacetato(α-5,7-η-3β-acetoxyandrostenyl-17-one)palladium(II)] (20), a new ring B π-allyl steroid–palladium complex, in quantitative yield. Thallium(III) trifluoroacetate gave 3β-acetoxy-5α-hydroxy-6β-trifluoroacetoxyandrostan-17-one (16), 3β-acetoxy-6β-trifluoroacetoxyandrost-4-en-17-one (9), 3β-acetoxy-4β-trifluoroacetoxyandrost-5-en-17-one (10), and 3β-acetoxy-5α,6β-dihydroxyandrostan-17-one (17). Lead(IV) trifluoroacetate yielded 9, 10 and 16. 3β-Acetoxy-5α,6β-bis(trifluoroacetoxy)androstan-17-one (15), a new compound, was also formed in this reaction. During the course of the lead(IV) studies the dichlorosteroid 21 and the rearranged allylic oxidation product 24 were formed. Their formation was attributed to the generation of lead(IV) chloride in the reaction. Silver(I) and copper(II) trifluoroacetates proved to be unreactive towards 6.

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