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Further studies on the selective oxidation of steroidal allylic alcohols

1984; Elsevier BV; Volume: 35; Issue: 4 Linguagem: Inglês

10.1016/0009-3084(84)90074-4

1873-2941

Edward J. Parish, Aubrey D. Scott, James R. Dickerson, Waite Dykes,

Chemical Reaction Mechanisms

Certain aromatic amines, when used in conjunction with pyridinium chlorochromate, have been found to selectively oxidize the allylic hydroxyl group of steroidal alcohols to the corresponding α,β-unsaturated ketones. In this respect, the amines 2,2′-bipyridine, 2,4,6-triphenyl-pyridinine, pyrazine, pyridazine and s-triazine were found to be effective in augmenting the rapid and selective oxidation of steroidal allylic alcohols. The reactions were carried out by the addition of the oxidant to a dry methylene chloride solution at 2°C containing an amine and an allylic alcohol.