A VERSATILE ROUTE TO SUBSTITUTED 1,4-DIAZINE-FUSED [60]FULLERENES

An alternative route to fullereno-C-60-I-h-[1,9-d]-2'-hydroxycyclohexa none (4a) is presented based on the [4 + 2] cycloaddition of 2,3-bis(t rimethylsiloxy)butadiene (3) and [60]fullerene. The oxidation of the p rimary monoadduct with bromine yield the new ]fullereno-C-60-I-h-[1,9- d]-1',2'-cyclohexanedione (5) which can be isolated as the dimethoxime derivative (9). The diketone 5 constitutes a versatile reactant for t he synthesis of different substituted -C-60-I-h-[1,9-b]-1',2',3',4'-te trahydrophenazines (6a-d). The isolation, characterization, controlled -temperature H-1 NMR measurements as well as UV-vis and fluorescence s tudies of these new heterocycles are presented.