Unfairly forgotten member of the iodocarborane family: Synthesis and structural characterization of 8-iodo-1,2-dicarba-closododecaborane, its precursors, and derivatives.

Inorganic Chemistry

Volumn 51, Issue 4, 2012, Pages 2629-2637

  Safronov, Alexander V ^a   Sevryugina, Yulia V ^a   Jalisatgi, Satish S ^a   Kennedy, Robert D ^b   Barnes, Charles L ^c   Hawthorne, M Frederick ^a  

^a University of Missouri   (United States)

^b NORTHWESTERN UNIVERSITY   (United States)

^c UNIVERSITY OF MISSOURI   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84857765685     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic2025846     Document Type: Article

References (47)

1. Wilbur, D. S. US Patent WO 9505202, 1995
2. Srivastava, R. R.; Hamlin, D. K.; Wilbur, D. S. J. Org. Chem. 1996, 61, 9041
3. Martin Jimenez, J.; Speck, U.; Carretero Colon, J. M.; Martinez Sans, A.; Bohle, F.; Krause, W. Patent EP 0700918A1, 1995.
4. Julius, R. L.; Farha, O. K.; Chiang, J.; Perry, L. J.; Hawthorne, M. F. Proc. Natl. Acad. Sci. U.S.A. 2007, 104, 4808.
5. Hawthorne, M. F.; Lee, M. W. J. Neurooncol. 2003, 62, 33
6. Hawthorne, M. F.; Shelly, K.; Li, F. Chem. Commun. 2002, 547
7. Hawthorne, M. F.; Maderna, A. Chem. Rev. 1999, 99, 3421.
8. For recent examples, see: Sevryugina, Y.; Julius, R. L.; Hawthorne, M. F. Inorg. Chem. 2010, 49, 10627
9. Aizawa, K.; Ohta, K.; Endo, Y. Heterocycles 2010, 80, 369
10. Himmelspach, A.; Finze, M. Eur. J. Inorg. Chem. 2010, 2012
11. Kabytaev, K. Z.; Mukhin, S. N.; Glukhov, I. V.; Starikova, Z. A.; Bregadze, V. I.; Beletskaya, I. P. Organometallics 2009, 28, 4758
12. Mukhin, S. N.; Kabytaev, K. Z.; Zhigareva, G. G.; Glukhov, I. V.; Starikova, Z. A.; Bregadze, V. I.; Beletskaya, I. P. Organometallics 2008, 27, 5937
13. Beletskaya, I. P.; Bregadze, V. I.; Ivushkin, V. A.; Petrovskii, P. V.; Sivaev, I. B.; Sjöberg, S.; Zhigareva, G. G. J. Organomet. Chem. 2004, 689, 2920.
14. For general information, see: Grimes, R. N. Carboranes, 2nd ed.; Academic Press: New York, 2011.
15. Puga, A. V.; Teixidor, F.; Sillanpää, R.; Kivekäs, R.; Viñas, C. Chem.-Eur. J. 2009, 15, 9764 and references therein.
16. Aufderheide, B. E.; Sprecher, R. F. Inorg. Chem. 1974, 13, 2286.
17. Gregor, V.; Stuchlík, J. Collect. Czech. Chem. Commun. 1973, 38, 3623
18. Zakharkin, L. I.; Kalinin, V. N.; Lozovskaya, V. S. Russ. Chem. Bull., Chem. Ser. 1968, 1780.
19. Yang, X.; Jiang, W.; Knobler, C. B.; Hawthorne, M. F. J. Am. Chem. Soc. 1992, 114, 9719.
20. Herzog, A.; Jalisatgi, S. S.; Knobler, C. B.; Wedge, T. J.; Hawthorne, M. F. Chem.-Eur. J. 2005, 11, 7155.
21. SAINT, v 7.68A; Bruker AXS Inc.: Madison, WI, 2009.
22. Sheldrick, G. M. SADABS 2008/1; Gottingen, Germany, 2008.
23. Sheldrick, G. M. SHELXTL, version 6.14; Bruker AXS, Inc.: Madison, WI, 2001.
24. Scobie, M.; Threadgill, M. D. J. Chem. Soc., Perkin Trans. 1 1994, 2059.
25. Safronov, A. V.; Hawthorne, M. F. Inorg. Chim. Acta 2011, 375, 308
26. Manning, M. J.; Knobler, C. B.; Hawthorne, M. F.; Do, Y. Inorg. Chem. 1991, 30, 3591.
27. Heying, T. L.; Ager, J. W. Jr.; Clark, S. L.; Mangold, D. J.; Oldstein, H. L.; Hillman, M.; Polak, R. J.; Szymanski, J. W. Inorg. Chem. 1963, 2, 1089
28. Fein, M. M.; Grafstein, D.; Paustian, J. E.; Bobinski, J.; Lichstein, B. M.; Mayes, N.; Schwartz, N. N.; Cohen, A. S. Inorg. Chem. 1963, 2, 1115.
29. Hillman, M. J. Am. Chem. Soc. 1960, 82, 1096.
30. In the Ph.D. thesis by B. E. Aufderheide (Synthesis, boron-11 NMR shift assignments and correlations for halogenated decaboranes, carboranes and derivatives, and thermal rearrangements of 1-phenyl-3-fluoro-o-carborane, Carnegie-Mellon University, 1975) the yield of product 9 (Scheme 2) was not specified. The reported yield of the 9 → 7 step was 60%.
31. Andrews, J. S.; Zayas, J.; Jones, M. Jr. Inorg. Chem. 1985, 24, 3715.
32. Marshall, W. J.; Young, R. J. Jr.; Grushin, V. V. Organometallics 2001, 20, 523.
33. Li, Y.; Carroll, P. J.; Sneddon, L. G. Inorg. Chem. 2008, 47, 9193.
34. Li, J.; Logan, C. F.; Jones, M. Jr. Inorg. Chem. 1991, 30, 4866.
35. Andrianov, V. G.; Stanko, V. I.; Struchkov, Yu. T.; Klimova, A. I. Zh. Strukt. Khim. 1967, 8, 707.
36. Bregadze, V. I. Chem. Rev. 1992, 92, 209
37. Kalinin, V. N.; Ol'shevskaya, V. A. Russ. Chem. Bull., Int. Ed. 2008, 57, 815.
38. Barberá, G.; Viñas, C.; Teixidor, F.; Rosair, G. M.;Welch, A. J. J. Chem. Soc., Dalton Trans. 2002, 3647
39. Fox, M. A.; Hughes, A. K. Coord. Chem. Rev. 2004, 248, 457.
40. Tomita, H.; Luu, H.; Onak, T. Inorg. Chem. 1991, 30, 812
41. Fox, M. A.; Gill, W. R.; Herbertson, P. L.; MacBride, J. A. H.; Wade, K. Polyhedron 1996, 15, 565
42. Yoo, J.; Hwang, J.-W.; Do, Y. Inorg. Chem. 2001, 40, 568.
43. Yamazaki, H.; Ohta, K.; Endo, Y. Tetrahedron Lett. 2005, 46, 3119.
44. For recent reviews on chemistry of metallacarboranes of transition metals, see: Corsini, M.; Fabrizi de Biani, F.; Zanello, P. Coord. Chem. Rev. 2006, 250, 1351
45. Chizhevsky, I. T. Coord. Chem. Rev. 2007, 251, 1590
46. Deng, L.; Xie, Z. Coord. Chem. Rev. 2007, 251, 2452
47. Xie, Z. Coord. Chem. Rev. 2002, 231, 23.