Synthesis of stable dodecaalkoxy derivatives of hypercloso-B 12H12

Journal of the American Chemical Society

Volumn 127, Issue 51, 2005, Pages 18243-18251

  Farha, Omar K ^a   Julius, Richard L ^a   Lee, Mark W ^a   Huertas, Ramon E ^a   Knobler, Carolyn B ^a   Hawthorne, M Frederick ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYLATION; ELECTRONS; ESTERS; ETHANOL; MIXTURES; OXIDATION; REACTION KINETICS; REDUCTION; SYNTHESIS (CHEMICAL); X RAY DIFFRACTION;

CHEMICAL OXIDATION; RADICAL ANIONS; REACTION MIXTURES; REFLUX TEMPERATURE;

DERIVATIVES;

ALCOHOL; ETHYLAMINE; ETHYLDIISOPROPYLAMINE; OXIDIZING AGENT; SODIUM BOROHYDRIDE; TOLUENESULFONAMIDE DERIVATIVE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; AUTOCLAVE; OXIDATION; SYNTHESIS; X RAY DIFFRACTION;

EID: 29844457868     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0556373     Document Type: Article

References (54)

1. (a) Pitochelli, A. R.; Hawthorne, M. F. J. Am. Chem. Soc: 1960, 82, 3228.
2. (b) Wunderlich, J. A.; Lipscomb, W. N. J. Am. Chem. Soc. 1960, 82, 4427.
3. (c) Longuet-Higgins, H. C.; Roberts, M. de V. Proc. R. Soc. London 1955, A230, 110.
4. (a) Hoffman, R.; Lipscomb, W. N. J. Chem. Phys. 1962, 38 (8), 2179.
5. (b) Hawthorne, M. F. Advances in Boron Chemistry; Special Publication No. 201; Royal Society of Chemistry: London, 1997; Vol. 82, p 261.
6. Peymann, T.; Herzog, A.; Knobler, C. B.; Hawthorne, M. F. Angew. Chem., Int. Ed. 1999, 38, 1062.
7. Bayer, M. J.; Hawthorne, M. F. Inorg. Chem. 2004, 43, 2018.
8. Peymann, T.; Knobler, C. B.; Khan, S. I.; Hawthorne, M. F. J. Am. Chem. Soc. 2001, 123, 2182.
9. Hawthorne, M. F.; Peymann, T.; Herzog, A. H. U.S. Patent 6.323.372. 2001.
10. Herzog, A.; Knobler, C. B.; Hawthorne, M. F. J. Am. Chem. Soc. 2001, 123, 12791.
11. Maderna, A.; Knobler, C. B.; Hawthorne, M. F. Angew. Chem., Int. Ed. 2001, 40, 1662.
12. Peymann, T.; Knobler C. B.; Khan S. I.; Hawthorne, M. F. Angew. Chem., Int. Ed. 2001, 40, 1664.
13. Thomas, J.; Hawthorne, M. F. Chem. Commun. 2001, 18, 1884.
14. Hawthorne, M. F. Pure Appl. Chem. 2003, 75, 1157.
15. Li, T.; Jalisatgi, S. S.; Bayer, M. J.; Maderna, A.; Khan, S. I.; Hawthorne, M. J. Am. Chem. Soc., in press.
16. Farha, O. K.; Lee, M. W.; Julius, R. L.; Hansch, C.; Hawthorne, M. F. J. Am. Chem. Soc., to be submitted for publication.
17. McKee, M. Inorg. Chem. 2002, 41, 1299.
18. Fujimori, M.; Kimura, K. J. Solid State Chem. 1997, 133, 178.
19. Wade, K. D. Adv. Inorg. Chem. Radiochem. 1976, 18, 1.
20. Peymann, T.; Knobler, C. B.; Hawthorne, M. F. Chem. Commun. 1999, 2039.
21. King, B. T.; Janousek, Z.; Gruener, B.; Trammell, M.; Noll, B. C.; Michl, J. J. Am. Chem. Soc. 1996, 118, 3313.
22. Morrison, J. Chem. Rev. 1991, 91, 35
23. Carter, F. L.; Siatkowski, R. E.; Wohljen, H. Molecular Electronic Devices; North-Holland: Amsterdam, 1988.
24. (a) Miedaner, A.; Curtis, C. J.; Barkley, R. M.; DuBois, D. L. Inorg. Chem. 1994, 33, 5482.
25. (b) Reetz, M. T.; Lohmer, G.; Schwickardi, R. Angew. Chem., Int. Ed. Engl. 1997, 36, 1526.
26. (c) Chow, H. F.; Mak, C. C. J. Org. Chem. 1997, 62, 5116.
27. (d) Bhyrappa, P.; Young, J. K.; Moore, J. S.; Suslick, K. S. J. Am. Chem. Soc. 1996, 118, 5708.
28. (a) Balzani, V.; Scandola, F. Suprumolecular Photochemistry; Horwood: Chichester, U.K., 1991.
29. (b) Lehn, J.-M. Supramalecular Chemistry; VCH: Weinheim. Germany, 1995.
30. Thomas, G. D. Methods Mol. Med. 2000, 25, 97.
31. Reddy, J. A.; Low, P. S. Crit. Rev. Ther. Drug Carrier Syst. 1998, 15, 587.
32. Haugland, R. P. Fluorescent Labels; Humana Press: Totowa, NJ, 1991.
33. Weiner, R. E.; Thakur, M. L. Radiochim. Acta 1995, 70-1, 273.
34. Buchsbaum, D. J. Cancer 1997, 80, 2371.
35. Hawthorne, M. F.; Maderna, A. Chem. Rev. 1999, 99, 3421.
36. Anderson, C. J.; Lewis, J. S. Expert Opin. Ther. Pat. 2000, 10, 1057.
37. Caravan, P.; Ellison, J. J.; McMurry, T. J.; Lauffer, R. B. Chem. Rev. 1999, 99, 2293.
38. Wender, P. A.; Mitchell, D. J.; Pattabiraman, K.; Pelkey, E. T.; Steinman, L.; Rothbard, J. B. Proc. Natl. Acad. Sci. U.S.A. 2000, 97, 13003.
39. Rajski, S. R.; Williams, R. M. Chem. Rev. 1998, 98, 2723.
40. Nilsson, F.; Tarli, L.; Viti, F.; Neri, D. Adv. Drug Delivery Rev. 2000, 43, 165.
41. Latham, P. W. Nat. Biotechnol. 1999, 17, 755.
42. Zanini, D.; Roy, R. Bioconjugate Chem. 1997, 8, 187.
43. Tam, J. P. Proc. Natl. Acad. Sci. U.S.A. 1988, 85, 5409.
44. Bielinska, A.; Kukowska-Latallo, J. F.; Johnson, J.; Tomalia, D. A.; Baker, J. R., Jr. Nucleic Acids Res. 1996, 24, 2176.
45. Shockley, T. R.; Lin, K. E.; Nagy, J. A.; Tompkins, R. G.; Dvorak, H. F.; Yarmush, M. L. Ann. N. Y. Acad. Sci. 1991, 618, 367.
46. George, A. J. T.; Urch, C. E. Diagnostic and Therapeutic Antibodies; Humana Press: Totowa, NJ. 2000.
47. Hawker, C. J.; Frèchet, J. M. J. J. Am. Chem. Soc. 1990, 112, 7638.
48. Tomalia, D. A.; Naylor, A. M.; Goddard, W. A., III. Angew. Chem., Int. Ed. Engl. 1990, 29, 138.
49. Knoth, W. H.; Sauer, J. C.; England, D. C.; Hertler, W. R.; Muetterties, E. L. J. Am. Chem. Soc. 1964, 86, 3973.
50. Peymann, T.; Knobler, C. B.; Hawthorne, M. F. Inorg. Chem. 2000, 39, 1163.
51. (a) Streitwieser, A. Chem. Rev. 1956, 56, 571.
52. (b) Streitwieser, A. Salvolytic Displacement Reactions; McGraw-Hill: New York, 1968.
53. (c) King, J. F.; Tsang, G. T. Y. J. Chem. Soc., Chem Commun. 1979, 1131.
54. Ganem, B.; Small Jr., V. R. J. Org. Chem. 1974, 39, 3728.