Selectivity of the Anodic Oxidation of CH‐ and CH₂‐Groups; Selective Oxidation of Steroids at C‐6

Abstract

Anodic oxidation results in comparatively good chemoselectivity; the ratio of attack at tertiary to attack at secondary C atoms is 12 : 1 for decalin. The regioselectivity of anodic oxidation may be controlled by inductive effects in the case of chlorides (e.g., chlorocyclohexane) and fatty acids. Remarkably, the steroids androstane and cholestane undergo oxidation mainly at C‐6.