On the oxidation of hydrazones by lead tetra-acetate

Abstract

The oxidation of 3β-hydroxylanostan-7-one hydrazone with lead tetra-acetate gave, after acetylation, 3β-acetoxylanost-7-ene and, as major product, 3β,7α-diacetoxylanostane. The corresponding oxidation of 3β-hydroxylanost-24-en-7-one hydrazone gave 3β-hydroxylanosta-7,24-diene and, as main product, 3β-hydroxy-7α-acetoxylanost-24-ene. The corresponding reactions of benzophenone hydrazone, dicyclohexyl ketone hydrazone, and camphor hydrazone were also investigated in order to examine the mechanism of the oxidation.

The related oxidations of benzophenone hydrazone and 3β-hydroxylanostan-7-one hydrazone with perbenzoic acid are also described.

The lead tetra-acetate oxidation of hydrazones is, in certain cases, a synthetically useful reaction.