Quelques aspects du mecanisme de l'oxydation anodique de quelques halogenures d'adamantyl-2

For the anodic oxidation in acetonitrile of some 2-adamantyl halides, the distribution of reaction products is dependent upon the halogen and substitution at the bridgehead positions. Iodides gave exclusively 2-adamantyl acetamides. 2-Chloroadamantane yields to chloroadamantyl acetamides. From bromides both 2-adamantyl acetamides and bromoadamantyl acetamides are formed. Part of the reaction products obtained with 2-fluoroadamantane are formed from the cleavage of C₂F bond; this result is explained by analogy with the mass spectrometric fragmentation behavior of this compound. A general reaction mechanism covering all our experimental results is proposed.