ELECTROCHEMISTRY OF HALOGENATED ADAMANTANE DERIVATIVES IN THE ABSENCE AND IN THE PRESENCE OF CO_2

摘要

This paper is concerned with the electrochemistry of mono- (2), (1,3) di- (3), (l,3,5)tri- (4) and (l,3,5,7)tetra- (5)Br substituted adamantane (1). When dissolved in Dimethylformamide, DMF, containing Et_4NClO_4 0.1M as supporting electrolyte, the compounds exhibit a regular shift of the reduction potential on glassy carbon (GC) electrode toward more negative values, in going from (2) to (5). This trend may be related to the peculiar structure of the rigid skeleton. Preparative experiments (controlled potential electrolyses) with and whithout added CO_2 furnish products stemming from dehydroadamantane and carbanionic derivatives.