United States Patent | 5,475,172 |
Cahill, et. al. | Dec. 12, 1995 |
Inventors: | Cahill; Paul A. (Albuquerque, NM); Henderson; Craig C. (Dublin, CA). |
Assignee: | Sandia Corporation (Albuquerque, NM). |
Appl. No.: | 160,345 |
Filed: | Dec. 1, 1993 |
Intl. Cl.: | C07C 1/00; C07C 13/62; C01B 31/00 |
U.S. Cl.: | 585/ 27; 585/ 22; 585/266; 585/271; 585/469; 585/943; 423/445.B |
Field of Search: | 423/445 B, DIG. 39, DIG. 40; 585/943, 22, 26, 27, 266, 271, 469 |
Chandrasekharan, S., "Organic Chemistry with Buckminsterfullerene (C(60))", Indian Journal of Chemistry, vol. 31 A and B, May 1992, pp. F36-F41.
Taylor et al., Nature., vol. 363 pp. 685-693 Jun. 24, 1993.
Welch et al., Journal of Chromatography vol. 609, pp. 89-101 Sep. 18, 1992.
Chiang et al., Journ. Am. Chem. Soc., 114(26) pp. 10154-10157 Dec. 16, 1992.
Chiang et al., Journ. Chem. Soc., Chem. Commun., No. 24, Dec. 15, 1992.
Ballenweg et al., Tetrahedron Letters, 34(23) pp. 3737-3740, Jun. 4, 1993.
Rao et al. [Indian Journal of Chemistry, vol. 31, pp. F27-F31, May 1993.
Schneider et al., J. Chem. Soc. Chem. Comm., pp. 463-464, Feb. 21, 1994.
Kroto, H. W., et al, Nature, "C(60) : Buckminsterfullerene," vol. 318, pp. 162-163, (Nov. 1985).
Kratschmer, W., et al, Nature, "Solid C(60) : A New Form of Carbon," vol. 347, pp. 354-358, (Sep. 1990).
Haufler, R. E., et al., J. Phys. Chem., "Efficient Production of C(60) (Buckminsterfullerene), C(60) H(36), and the Solvated Buckide Ion," vol. 94, pp. 8634-8636, (1990).
Taylor, R., J. Chem. Soc. Perkin Trans. 2, "C(60), C(70), C(76), C(78), C(84) : Numbering, .pi.-Bond Order Calculations and Addition Pattern Considerations," pp. 813-824, (1993).
Friedman, et al., J. Am. Chem. Soc., "Inhibition of the HIV-1 Protease by Fullerene Derivatives: Model Building Studies and Experimental Verification," vol. 115, pp. 6506-6509, (1993).
Sijbesma, R., et al. J. Am. Chem. Soc., "Synthesis of a Fullerene Derivative for the Inhibition of HIV Enzymes," vol. 115, pp. 6510-6512, (1993).
Schinazi, R. F. et al, Antimicrobial Agents and Chemotherapy, "Synthesis and Virucidal Activity of a Water-Soluble, Configurationally Stable, Derivatized C(60) Fullerene," vol. 37, No. 8, pp. 1707-1710, (Aug., 1993).
Welch, C. J. et al, Journal of Chromatography, "Progress In The Design of Selectors For Buckminsterfullene," vol. 609, pp. 89-101, (1992).
Baum, R., Chemical and Engineering News, "Fullerene Bioactivity C(60) Derivative Inhibits AIDS Viruses," pp. 3-4, (aug. 1993).
Di-addended and tetra-addended Buckminster fullerenes are synthesized through the use of novel organoborane intermediates. The C(60), C(70), or higher fullerene is reacted with a borane such as BH(3) in a solvent such as toluene to form an organoborane intermediate. Reaction of the organoborane such as hydrolysis with water or alcohol results in the product di-addended and tetra-addended fullerene in up to 30% yields. Dihydrofullerenes and tetrahydrofullerenes are produced by the process of the invention.
The United States Government has rights in this invention pursuant to Contract No. DE-AC04-76DP00789 between the Department of Energy and American Telephone and Telegraph Company.