Unwinding antiaromaticity in 1-bromo-2,3,4,5-tetraphenylborole

Organometallics

Volumn 30, Issue 11, 2011, Pages 3210-3216

  Braunschweig, Holger ^a   Chiu, Ching Wen ^a,b   Damme, Alexander ^a   Ferkinghoff, Katharina ^a   Kraft, Katharina ^a   Radacki, Krzysztof ^a   Wahler, Johannes ^a  

^a UNIVERSITY OF WÜRZBURG   (Germany)

^b NATIONAL TAIWAN UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIAROMATIC CHARACTER; ANTIAROMATICITY; B FRAMEWORK; CARBENES; ISOLATION AND CHARACTERIZATION; ISOSTRUCTURAL; LEWIS ACID-BASE ADDUCTS; REARRANGEMENT REACTIONS; SINGLE CRYSTAL X-RAY DIFFRACTION; TITLE COMPOUNDS;

ORGANIC COMPOUNDS; SYNTHESIS (CHEMICAL); X RAY DIFFRACTION;

X RAY CRYSTALLOGRAPHY;

EID: 79958134823     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om200315p     Document Type: Article

References (62)

1. Eisch, J. J.; Galle, J. E.; Kozima, S. J. Am. Chem. Soc. 1986, 108, 379.
2. Hückel, E. Grundzüge der Theorie Ungesättigter und Aromatischer Verbindungen; Verlag Chemie: Berlin, 1938.
3. Breslow, R. Chem. Eng. News. 1965, 43, 90.
4. Breslow, R. Acc. Chem. Res. 1973, 6, 393.
5. Eisch, J. J.; Hota, N. K.; Kozima, S. J. Am. Chem. Soc. 1969, 91, 4575.
6. Braunschweig, H.; Fernandez, I.; Frenking, G.; Kupfer, T. Angew. Chem., Int. Ed. 2008, 47, 1951.
7. So, C. W.; Watanabe, D.; Wakamiya, A.; Yamaguchi, S. Organometallics 2008, 27, 3496.
8. Braunschweig, H.; Kupfer, T. Chem. Commun. 2008, 4487.
9. Fan, C.; Piers, W. E.; Parvez, M. Angew. Chem., Int. Ed. 2009, 48, 2955.
10. Braunschweig, H.; Chiu, C.-W.; Radacki, K.; Brenner, P. Chem. Commun. 2010, 46, 916.
11. Braunschweig, H.; Breher, F.; Chiu, C.-W.; Gamon, D.; Nied, D.; Radacki, K. Angew. Chem., Int. Ed. 2010, 49, 8975.
12. Braunschweig, H.; Chiu, C.-W.; Radacki, K.; Kupfer, T. Angew. Chem., Int. Ed. 2010, 49, 2041.
13. Steffen, A.; Ward, R. M.; Jones, W. D.; Marder, T. B. Coord. Chem. Rev. 2010, 254, 1950.
14. Braunschweig, H.; Chiu, C.-W.; Wahler, J.; Radacki, K.; Kupfer, T. Chem.-Eur. J. 2010, 16, 12229.
15. Köhler, J.; Lindenmeier, S.; Fischer, I.; Braunschweig, H.; Kupfer, T.; Gamon, D.; Chiu, C.-W. J. Raman Spectrosc. 2010, 41, 636.
16. Fan, C.; Piers, W. E.; Parvez, M.; McDonald, R. Organometallics 2010, 29, 5132.
17. Fan, C.; Mercier, L. G.; Piers, W. E.; Tuononen, H. M.; Parvez, M. J. Am. Chem. Soc. 2010, 132, 9604.
18. Ansorg, K.; Braunschweig, H.; Chiu, C.-W.; Engels, B.; Gamon, D.; Hügel, M.; Kupfer, T.; Radacki, K. Angew. Chem., Int. Ed. 2011, 50, 2833.
19. Cao, H.; Ma, J.; Zhang, G.; Jiang, Y. Macromolecules 2005, 38, 1123.
20. Yuan, Z.; Taylor, N. J.; Sun, Y.; Marder, T. B.; Williams, I. D.; Cheng, L. T. J. Organomet. Chem. 1993, 449, 27.
21. Weber, L.; Werner, V.; Fox, M. A.; Marder, T. B.; Schwedler, S.; Brockhinke, A.; Stammler, H. G.; Neumann, B. Dalton Trans. 2009, 1339.
22. Lorbach, A.; Bolte, M.; Li, H.; Lerner, H. W.; Holthausen, M. C.; Jaekle, F.; Wagner, M. Angew. Chem., Int. Ed. 2009, 48, 4584.
23. Sundararaman, A.; Victor, M.; Varughese, R.; Jaekle, F. J. Am. Chem. Soc. 2005, 127, 13748.
24. Kim, S.; Song, K. H.; Kang, S. O.; Ko, J. Chem. Commun. 2004, 68.
25. Wakamiya, A.; Mishima, K.; Ekawa, K.; Yamaguchi, S. Chem. Commun. 2008, 579.
26. Yamaguchi, S.; Shirasaka, T.; Akiyama, S.; Tamao, K. J. Am. Chem. Soc. 2002, 124, 8816.
27. Wade, C. R.; Gabbai, F. P. Inorg. Chem. 2010, 49, 714.
28. Wade, C. R.; Gabbai, F. P. Dalton Trans. 2009, 9169.
29. Yamaguchi, S.; Akiyama, S.; Tamao, K. J. Am. Chem. Soc. 2001, 123, 11372.
30. Chase, P. A.; Piers, W. E.; Patrick, B. O. J. Am. Chem. Soc. 2000, 122, 12911.
31. Chen, E. Y.-X.; Marks, T. J. Chem. Rev. 2000, 100, 1391.
32. Ishihara, K.; Yamamoto, H. Eur. J. Org. Chem. 1999, 527.
33. Herberich, G. E.; Buller, B.; Hessner, B.; Oschmann, W. J. Organomet. Chem. 1980, 195, 253.
34. Herberich, G. E.; Hengesbach, J.; Kölle, U.; Oschmann, W. Angew. Chem., Int. Ed. Engl. 1977, 16, 42.
35. Herberich, G. E.; Englert, U; Hostalek, M.; Laven, R. Chem. Ber. 1991, 124, 17.
36. Herberich, G. E.; Negele, M.; Ohst, H. Chem. Ber. 1991, 124, 25.
37. Gleiter, R.; Hyla-Kryspin, I.; Herberich, G. E. J. Organomet. Chem. 1994, 478, 95, and references therein.
38. Eisch, J. J.; Galle, J. E. J. Am. Chem. Soc. 1975, 97, 4436.
39. Eisch, J. J.; Galle, J. E. J. Organomet. Chem. 1977, 127, C9.
40. Eisch, J. J.; Galle, J. E.; Shafii, B.; Rheingold, A. L. Organometallics 1990, 9, 2342.
41. Fagan, P. J.; Burns, E. G.; Calabrese, J. C. J. Am. Chem. Soc. 1988, 110, 2979.
42. Braunschweig, H.; Ghosh, S.; Kupfer, T.; Radacki, K.; Wahler, J. Chem.-Eur. J. 2011, 17, 4081.
43. Killian, L.; Wrackmeyer, B. J. Organomet. Chem. 1978, 148, 137.
44. Nöth, H.; Wrackmeyer, B. Nuclear Magnetic Resonance Spectroscopy of Boron Compounds; Springer Verlag: Berlin, 1978; pp 129-133.
45. Braunschweig, H.; Radacki, K.; Rais, D.; Whittell, G. R. Angew. Chem., Int. Ed. 2005, 44, 1192.
46. Bats, J. W.; Urschel, B. Acta Crystallogr., Sect. E: Struct. Rep. Online 2006, E62, o748.
47. Uttinger, K. Synthesis, Structure and Reactivity of Late Transition Metal Boryl and Borylene Complexes; Julius-Maximilians-Universität: Würzburg, 2008.
48. Iijima, K.; Oonishi, I.; Shibata, S. Chem. Lett. 1983, 251.
49. Brown, H. C.; Ramachandran, P. V. J. Org. Chem. 1989, 54, 4504.
50. Weinmann, M.; Nuss, J.; Jansen, M. Acta Crystallogr., Sect. E: Struct. Rep. Online 2006, E62, o5590.
51. Saraev, V. V.; Kraikivskii, P. B.; Svoboda, I.; Kuzakov, A. S.; Jordan, R. F. J. Phys. Chem. A 2008, 112, 12449.
52. Cross, W. I.; Lightfoot, M. P.; Mair, F. S.; Pritchard, R. G. Inorg. Chem. 2000, 39, 2690.
53. Wagner, T.; Eigendorf, U.; Herberich, G. E.; Englert, U. Struct. Chem. 1994, 5, 233.
54. Bula, M. J.; Hamilton, D. E.; Hartman, J. S. J. Chem. Soc., Dalton Trans. 1972, 1405.
55. Hamilton, D. E.; Hartman, J. S.; Miller, J. M. Chem. Commun. 1969, 1417.
56. Fratiello, A.; Onak, T. P.; Schuster, R. E. J. Am. Chem. Soc. 1968, 90, 1194.
57. Hunt, R. L.; Ault, B. S. Spectroscopy 1982, 1, 45.
58. Guindon, Y.; Yoakim, C.; Morton, H. E. Tetrahedron Lett. 1983, 24, 2969.
59. Guindon, Y.; Therien, M.; Girard, Y.; Yoakim, C. J. Org. Chem. 1987, 52, 1680.
60. Issleib, K.; Brack, A. Z. Anorg. Allg. Chem. 1954, 277, 258.
61. Arduengo, A. J., III; Krafczyk, R.; Schmutzler, R.; Craig, H. A.; Goerlich, J. R.; Marshall, W. J.; Unverzagt, M. Tetrahedron 1999, 55, 14523.
62. Lavallo, V.; Canac, Y.; Präsang, C.; Donnadieu, B.; Bertrand, G. Angew. Chem., Int. Ed. 2005, 44, 5705.