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The Reactivity of C60 in Fuming Sulfuric and Chlorosulfonic Acids

  • G.P. Miller (a1), M.A. Buretea (a1), J.W. Swirczewski (a1) and J.M. McConnachie (a1)

Abstract

C60 is sultonated in fuming sulfuric acid and chlorinated in chlorosulfonic acid. Both reactions involve initial oxidation of C60 followed by in situ trapping of electrophilic C60 cation.

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References

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1. Xie, Q., Perez-Cordero, E. and Echegoyen, L. J. Am. Chem. Soc., 1992, 114, 3978.
2. See for example: (a) Penicaud, A., Hsu, J. and Reed, C.A. J. Am. Chem. Soc. 1991, 113, 6698; (b) Stinchcombe, J., Penicaud, A., Bhyrappa, P., Boyd, P.D.W. and Reed, C.A. J. Am. Chem. Soc. 1993, 115, 5212; (c) Fullagar, W.K., Gentle, I.R., Heath, G.A. and White, J.W. J. Chem. Soc., Chem. Comm. 1993, 525.
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8. Miller, G.P., Buretea, M.A., Bernardo, M.M., Hsu, C.S. and Fang, H.L. J. Chem. Soc., Chem. Comm. 1994, in press.
9. Miller, G.P., Swirczewski, J.W., Buretea, M.A. and McConnachie, J.M. Tett. Lett. 1994, submitted.
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12. Elemental analysis on fully hydrated 1 performed by Quantitative Technologies Incorporated, Whitehouse, New Jersey. Found: 55.37% C, 13.02% S, 1.29% H; TGA: 12.0% H2O. Calculated for C60(SO3)5.30·(H2O)8.69: 55.37% C, 13.06% S, 1.34% H, 12.03% H2O.
13. Birkett, P.R., Avent, A.G., Darwish, A.D., Kroto, H.W., Taylor, R. and Walton, D.R.M. J. Chem. Soc., Chem. Comm. 1993, 1230.
14. Hirsch, A., Li, Q. and Wudl, F. Angew. Chem. Int. Ed. Eng. 1991, 30, 1309.
15. Miller, G.P., Millar, J.M., Liang, B., Uldrich, S. and Johnston, J.E. J. Chem. Soc., Chem. Comm. 1993, 897.

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