

ELECTROCHEMICAL OXIDATIVE AROMATIZATION OF 9-SUBSTITUTED 9,10-DIHYDROACRIDINES: CLEAVAGE OF C–H vs C–X BOND

Abstract
Reactivity of dihydroacridines bearing a С–X fragment at the geminal C-9 atom (where X = C, N, O, P, S) on anode has been investigated by means of electrochemical oxidation and thermodynamic and quantum-chemical calculations. The electrochemical oxidation results either in the formation of the 9-substituted acridines or in the cleavage of the C–X bond. This dual behavior of dihydroazines is analogous to processes reported in literature that take place upon treatment with chemical oxidants.
Keywords
acridines; dihydroacridines; bond dissociation energy; C–H functionalization; electrochemical oxidation; SNH reactions; thermodynamic studies
Latvian Institute of Organic Synthesis - Aizkraukles iela, 21, Riga, LV-1006, Latvia - hgs@osi.lv