A versatile route to substituted 1,4-diazine-fused [60]fullerenes

Torres-Garcia G, Luftmann H, Wolff C, Mattay J. A versatile route to substituted 1,4-diazine-fused [60]fullerenes. The Journal of Organic Chemistry. 1997;62(9):2752-2756.An alternative route to [5,6]fullereno-C-60-I-h-[1,9-d]-2'-hydroxycyclohexanone (4a) is presented based on the [4 + 2] cycloaddition of 2,3-bis(trimethylsiloxy)butadiene (3) and [60]fullerene. The oxidation of the primary monoadduct with bromine yield the new [5,6]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 the synthesis of different substituted [5,6]fullereno-C-60-I-h-[1,9-b]-1',2',3',4'-tetrahydrophenazines (6a-d). The isolation, characterization, controlled-temperature H-1 NMR measurements as well as UV-vis and fluorescence studies of these new heterocycles are presented