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

Torres-Garcia G, Luftmann H, Wolff C, Mattay J (1997)
The Journal of Organic Chemistry 62(9): 2752-2756.

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Abstract
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.
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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.
Torres-Garcia, G., Luftmann, H., Wolff, C., & Mattay, J. (1997). A versatile route to substituted 1,4-diazine-fused [60]fullerenes. The Journal of Organic Chemistry, 62(9), 2752-2756.
Torres-Garcia, G., Luftmann, H., Wolff, C., and Mattay, J. (1997). A versatile route to substituted 1,4-diazine-fused [60]fullerenes. The Journal of Organic Chemistry 62, 2752-2756.
Torres-Garcia, G., et al., 1997. A versatile route to substituted 1,4-diazine-fused [60]fullerenes. The Journal of Organic Chemistry, 62(9), p 2752-2756.
G. Torres-Garcia, et al., “A versatile route to substituted 1,4-diazine-fused [60]fullerenes”, The Journal of Organic Chemistry, vol. 62, 1997, pp. 2752-2756.
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. 62, 2752-2756 (1997).
Torres-Garcia, G, Luftmann, H, Wolff, C, and Mattay, Jochen. “A versatile route to substituted 1,4-diazine-fused [60]fullerenes”. The Journal of Organic Chemistry 62.9 (1997): 2752-2756.
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Yao J, Xiao Z, Zhang J, Yang X, Gan L, Zhang WX., Chem. Commun. (Camb.) (4), 2009
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Polyarene-functionalized fullerenes in carbon nanotubes: towards controlled geometry of molecular chains.
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PMID: 19003823

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