Electrochemical difunctionalisation of adamantane and further oxidation of substituted adamantanes

Abstract

Anodic oxidation of adamantane in trifluoroacetic acid at a potential shown by cyclic voltammetry to be in the second wave, gives after hydrolytic work up adamantane-1,3-diol (70%). Similar oxidation in acetonitrile gives NN′-adamantane-1,3-diyl)bisacetamide (58%). Electroanalytical techniques are used to define the oxidation mechanism, and oxidations of some substituted adamantanes at high anodic potentials are described.