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- W1567158154 abstract "Oxidation of 3-substituted 5α-cholestan-2α,5-episulphides (4a, 4b, 5, 6a, 6b, 10a, and 10b) with m-chloroperbenzoic acid afforded the corresponding anti-sulphoxides (7a, 7b, 8, 9a, 9b, 11a, and 11b, respectively). Sulphinyl configurations have been assigned from chemical evidence and established by dipole-moments and NMR spectroscopy, 3β-Bromo-anti-sulphoxide 11a with phenyl lithium was found to give cholesta-2,4-diene. A mechanism is discussed which involves the formation of 5-(S)-phenylsulphinyl-5α-cholest-2-ene as an incipient intermediate, followed by syn-elimination via a cyclic intramolecular mechanism. Anisotropie shielding effects and benzene-induced solvent shifts concerning the S → O bond introduced are discussed." @default.
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- W1567158154 date "1972-01-01" @default.
- W1567158154 modified "2023-09-27" @default.
- W1567158154 title "Thiosteroids-XXXII" @default.
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- W1567158154 doi "https://doi.org/10.1016/0040-4020(72)80113-3" @default.
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