Diverse structures and remarkable oxidizing ability of triarylbismuthane oxides. Comparative study on the structure and reactivity of a series of triarylpnictogen oxides

Organometallics

Volumn 23, Issue 23, 2004, Pages 5471-5480

  Matano, Yoshihiro ^a   Nomura, Hazumi ^a   Hisanaga, Teppei ^a   Nakano, Haruyuki ^c   Shiro, Motoo ^b   Imahori, Hiroshi ^a  

^a KYOTO UNIVERSITY   (Japan)

^b KYUSHU UNIVERSITY   (Japan)

^c RIGAKU CORPORATION   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; CHEMICAL BONDS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROBABILITY DENSITY FUNCTION; PYROLYSIS; STRUCTURE (COMPOSITION); THERMODYNAMICS; THERMOOXIDATION; X RAY CRYSTALLOGRAPHY;

DATA COLLECTION PARAMETERS; LIGANDS; MILD CONDITIONS; OXIDIZING ABILITY;

REACTION KINETICS;

EID: 9144232387     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om0494115     Document Type: Article

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35. Many attempts to prepare triarylbismuthane oxides have been unsuccessful, (a) Challenger, F.; Goddard, A. E. J. Chem. Soc. 1920, 117, 762-773. (b) Monagle, J. J. J. Org. Chem. 1962, 27, 3851-3855. (c) Agolini, F.; Bonnett, R. Can. J. Chem. 1962, 40, 181-183. ( Bernstein, J.; Halman, M.; Pinchaa, S.; Samuel, D. J. Chem. Soc. 1964, 821-824. (e) Davies, A. G.; Hook, S. C. W. J. Chem. Soc. C1971, 1660-1665. (f) Brandes, D.; Blaschette, A. J. Organomet. Chem. 1974, 73, 217-227. (g) Glidewell, C. J. Organomet. Chem. 1976, 116, 199-209. (h) El Sheikh, S. I. A.; Patel, M. S.j Smith, B. C.; Waller, C. B. J. Chem. Soc., Dation Trans. 1977, 641-644. Suzuki, H.; Ikegami, T.; Matano, Y.; Azuma, N. J. Chem. Soc., Perkin Trans. 1 1993, 2411-2415.
36. Many attempts to prepare triarylbismuthane oxides have been unsuccessful, (a) Challenger, F.; Goddard, A. E. J. Chem. Soc. 1920, 117, 762-773. (b) Monagle, J. J. J. Org. Chem. 1962, 27, 3851-3855. (c) Agolini, F.; Bonnett, R. Can. J. Chem. 1962, 40, 181-183. ( Bernstein, J.; Halman, M.; Pinchaa, S.; Samuel, D. J. Chem. Soc. 1964, 821-824. (e) Davies, A. G.; Hook, S. C. W. J. Chem. Soc. C1971, 1660-1665. (f) Brandes, D.; Blaschette, A. J. Organomet. Chem. 1974, 73, 217-227. (g) Glidewell, C. J. Organomet. Chem. 1976, 116, 199-209. (h) El Sheikh, S. I. A.; Patel, M. S.j Smith, B. C.; Waller, C. B. J. Chem. Soc., Dation Trans. 1977, 641-644. Suzuki, H.; Ikegami, T.; Matano, Y.; Azuma, N. J. Chem. Soc., Perkin Trans. 1 1993, 2411-2415.
37. Many attempts to prepare triarylbismuthane oxides have been unsuccessful, (a) Challenger, F.; Goddard, A. E. J. Chem. Soc. 1920, 117, 762-773. (b) Monagle, J. J. J. Org. Chem. 1962, 27, 3851-3855. (c) Agolini, F.; Bonnett, R. Can. J. Chem. 1962, 40, 181-183. ( Bernstein, J.; Halman, M.; Pinchaa, S.; Samuel, D. J. Chem. Soc. 1964, 821-824. (e) Davies, A. G.; Hook, S. C. W. J. Chem. Soc. C1971, 1660-1665. (f) Brandes, D.; Blaschette, A. J. Organomet. Chem. 1974, 73, 217-227. (g) Glidewell, C. J. Organomet. Chem. 1976, 116, 199-209. (h) El Sheikh, S. I. A.; Patel, M. S.j Smith, B. C.; Waller, C. B. J. Chem. Soc., Dation Trans. 1977, 641-644. Suzuki, H.; Ikegami, T.; Matano, Y.; Azuma, N. J. Chem. Soc., Perkin Trans. 1 1993, 2411-2415.
38. Many attempts to prepare triarylbismuthane oxides have been unsuccessful, (a) Challenger, F.; Goddard, A. E. J. Chem. Soc. 1920, 117, 762-773. (b) Monagle, J. J. J. Org. Chem. 1962, 27, 3851-3855. (c) Agolini, F.; Bonnett, R. Can. J. Chem. 1962, 40, 181-183. ( Bernstein, J.; Halman, M.; Pinchaa, S.; Samuel, D. J. Chem. Soc. 1964, 821-824. (e) Davies, A. G.; Hook, S. C. W. J. Chem. Soc. C1971, 1660-1665. (f) Brandes, D.; Blaschette, A. J. Organomet. Chem. 1974, 73, 217-227. (g) Glidewell, C. J. Organomet. Chem. 1976, 116, 199-209. (h) El Sheikh, S. I. A.; Patel, M. S.j Smith, B. C.; Waller, C. B. J. Chem. Soc., Dation Trans. 1977, 641-644. Suzuki, H.; Ikegami, T.; Matano, Y.; Azuma, N. J. Chem. Soc., Perkin Trans. 1 1993, 2411-2415.
39. Many attempts to prepare triarylbismuthane oxides have been unsuccessful, (a) Challenger, F.; Goddard, A. E. J. Chem. Soc. 1920, 117, 762-773. (b) Monagle, J. J. J. Org. Chem. 1962, 27, 3851-3855. (c) Agolini, F.; Bonnett, R. Can. J. Chem. 1962, 40, 181-183. ( Bernstein, J.; Halman, M.; Pinchaa, S.; Samuel, D. J. Chem. Soc. 1964, 821-824. (e) Davies, A. G.; Hook, S. C. W. J. Chem. Soc. C1971, 1660-1665. (f) Brandes, D.; Blaschette, A. J. Organomet. Chem. 1974, 73, 217-227. (g) Glidewell, C. J. Organomet. Chem. 1976, 116, 199-209. (h) El Sheikh, S. I. A.; Patel, M. S.j Smith, B. C.; Waller, C. B. J. Chem. Soc., Dation Trans. 1977, 641-644. Suzuki, H.; Ikegami, T.; Matano, Y.; Azuma, N. J. Chem. Soc., Perkin Trans. 1 1993, 2411-2415.
40. Many attempts to prepare triarylbismuthane oxides have been unsuccessful, (a) Challenger, F.; Goddard, A. E. J. Chem. Soc. 1920, 117, 762-773. (b) Monagle, J. J. J. Org. Chem. 1962, 27, 3851-3855. (c) Agolini, F.; Bonnett, R. Can. J. Chem. 1962, 40, 181-183. ( Bernstein, J.; Halman, M.; Pinchaa, S.; Samuel, D. J. Chem. Soc. 1964, 821-824. (e) Davies, A. G.; Hook, S. C. W. J. Chem. Soc. C1971, 1660-1665. (f) Brandes, D.; Blaschette, A. J. Organomet. Chem. 1974, 73, 217-227. (g) Glidewell, C. J. Organomet. Chem. 1976, 116, 199-209. (h) El Sheikh, S. I. A.; Patel, M. S.j Smith, B. C.; Waller, C. B. J. Chem. Soc., Dation Trans. 1977, 641-644. Suzuki, H.; Ikegami, T.; Matano, Y.; Azuma, N. J. Chem. Soc., Perkin Trans. 1 1993, 2411-2415.
41. Many attempts to prepare triarylbismuthane oxides have been unsuccessful, (a) Challenger, F.; Goddard, A. E. J. Chem. Soc. 1920, 117, 762-773. (b) Monagle, J. J. J. Org. Chem. 1962, 27, 3851-3855. (c) Agolini, F.; Bonnett, R. Can. J. Chem. 1962, 40, 181-183. ( Bernstein, J.; Halman, M.; Pinchaa, S.; Samuel, D. J. Chem. Soc. 1964, 821-824. (e) Davies, A. G.; Hook, S. C. W. J. Chem. Soc. C1971, 1660-1665. (f) Brandes, D.; Blaschette, A. J. Organomet. Chem. 1974, 73, 217-227. (g) Glidewell, C. J. Organomet. Chem. 1976, 116, 199-209. (h) El Sheikh, S. I. A.; Patel, M. S.j Smith, B. C.; Waller, C. B. J. Chem. Soc., Dation Trans. 1977, 641-644. Suzuki, H.; Ikegami, T.; Matano, Y.; Azuma, N. J. Chem. Soc., Perkin Trans. 1 1993, 2411-2415.
42. Many attempts to prepare triarylbismuthane oxides have been unsuccessful, (a) Challenger, F.; Goddard, A. E. J. Chem. Soc. 1920, 117, 762-773. (b) Monagle, J. J. J. Org. Chem. 1962, 27, 3851-3855. (c) Agolini, F.; Bonnett, R. Can. J. Chem. 1962, 40, 181-183. ( Bernstein, J.; Halman, M.; Pinchaa, S.; Samuel, D. J. Chem. Soc. 1964, 821-824. (e) Davies, A. G.; Hook, S. C. W. J. Chem. Soc. C1971, 1660-1665. (f) Brandes, D.; Blaschette, A. J. Organomet. Chem. 1974, 73, 217-227. (g) Glidewell, C. J. Organomet. Chem. 1976, 116, 199-209. (h) El Sheikh, S. I. A.; Patel, M. S.j Smith, B. C.; Waller, C. B. J. Chem. Soc., Dation Trans. 1977, 641-644. Suzuki, H.; Ikegami, T.; Matano, Y.; Azuma, N. J. Chem. Soc., Perkin Trans. 1 1993, 2411-2415.
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46. -1 in the IR spectrum.
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48. (a) Pasenok, S. V.; Kirij, N. V.; Yagupolskii, Y. L.; Naumann, D.; Tyrra, W. J. Fluorine Chem. 1993, 63, 179-183.
49. (b) Matano, Y.; Nomura, H.; Suzuki, H.; Shiro, M.; Nakano, H. J. Am. Chem. Soc. 2001, 123, 10954-10965.
50. Pentavalent organobismuth compounds have been used as oxidizing agents. For example, see: (a) Barton, D. H. R.; Kitchin, J. P.; Lester, D. J.; Motherwell, W. B.; Papoula, M. T. B. Tetrahedron 1981, 37 (Supplement 1), 73-79. (b) Dodonov, V. A.; Gushchin, A. V.; Brilkina, T. G. J. Gen. Chem. USSR 1985, 55, 63-68; Zh. Obshch. Khim. 1985, 55, 73-80. Barton, D. H. R.; Yadav-Bhatnagar, N.; Finet, J.-P.; Khamsi, J.; Motherwell, W. B.; Stanforth, S. P. Tetrahedron 1987, 43, 323-332. Matano, Y.; Nomura, H. Angew. Chem., Int. Ed. 2002, 41, 3028-3031. (e) Komatsu, N. In Organobismuth Chemistry; Suzuki, H., Matano, Y. Eds.; Elsevier: New York, 2001; Chapter 5, pp 371-440. (f) Matano, Y. In Main Group Metals in Organic Synthesis; Yamamoto, H., Oshima, K., Eds.; Wiley-VCH: Weinheim, Germany, 2004; Chapter 14, pp 753-811, and references therein.
51. Pentavalent organobismuth compounds have been used as oxidizing agents. For example, see: (a) Barton, D. H. R.; Kitchin, J. P.; Lester, D. J.; Motherwell, W. B.; Papoula, M. T. B. Tetrahedron 1981, 37 (Supplement 1), 73-79. (b) Dodonov, V. A.; Gushchin, A. V.; Brilkina, T. G. J. Gen. Chem. USSR 1985, 55, 63-68; Zh. Obshch. Khim. 1985, 55, 73-80. Barton, D. H. R.; Yadav-Bhatnagar, N.; Finet, J.-P.; Khamsi, J.; Motherwell, W. B.; Stanforth, S. P. Tetrahedron 1987, 43, 323-332. Matano, Y.; Nomura, H. Angew. Chem., Int. Ed. 2002, 41, 3028-3031. (e) Komatsu, N. In Organobismuth Chemistry; Suzuki, H., Matano, Y. Eds.; Elsevier: New York, 2001; Chapter 5, pp 371-440. (f) Matano, Y. In Main Group Metals in Organic Synthesis; Yamamoto, H., Oshima, K., Eds.; Wiley-VCH: Weinheim, Germany, 2004; Chapter 14, pp 753-811, and references therein.
52. Pentavalent organobismuth compounds have been used as oxidizing agents. For example, see: (a) Barton, D. H. R.; Kitchin, J. P.; Lester, D. J.; Motherwell, W. B.; Papoula, M. T. B. Tetrahedron 1981, 37 (Supplement 1), 73-79. (b) Dodonov, V. A.; Gushchin, A. V.; Brilkina, T. G. J. Gen. Chem. USSR 1985, 55, 63-68; Zh. Obshch. Khim. 1985, 55, 73-80. Barton, D. H. R.; Yadav-Bhatnagar, N.; Finet, J.-P.; Khamsi, J.; Motherwell, W. B.; Stanforth, S. P. Tetrahedron 1987, 43, 323-332. Matano, Y.; Nomura, H. Angew. Chem., Int. Ed. 2002, 41, 3028-3031. (e) Komatsu, N. In Organobismuth Chemistry; Suzuki, H., Matano, Y. Eds.; Elsevier: New York, 2001; Chapter 5, pp 371-440. (f) Matano, Y. In Main Group Metals in Organic Synthesis; Yamamoto, H., Oshima, K., Eds.; Wiley-VCH: Weinheim, Germany, 2004; Chapter 14, pp 753-811, and references therein.
53. Pentavalent organobismuth compounds have been used as oxidizing agents. For example, see: (a) Barton, D. H. R.; Kitchin, J. P.; Lester, D. J.; Motherwell, W. B.; Papoula, M. T. B. Tetrahedron 1981, 37 (Supplement 1), 73-79. (b) Dodonov, V. A.; Gushchin, A. V.; Brilkina, T. G. J. Gen. Chem. USSR 1985, 55, 63-68; Zh. Obshch. Khim. 1985, 55, 73-80. Barton, D. H. R.; Yadav-Bhatnagar, N.; Finet, J.-P.; Khamsi, J.; Motherwell, W. B.; Stanforth, S. P. Tetrahedron 1987, 43, 323-332. Matano, Y.; Nomura, H. Angew. Chem., Int. Ed. 2002, 41, 3028-3031. (e) Komatsu, N. In Organobismuth Chemistry; Suzuki, H., Matano, Y. Eds.; Elsevier: New York, 2001; Chapter 5, pp 371-440. (f) Matano, Y. In Main Group Metals in Organic Synthesis; Yamamoto, H., Oshima, K., Eds.; Wiley-VCH: Weinheim, Germany, 2004; Chapter 14, pp 753-811, and references therein.
54. Pentavalent organobismuth compounds have been used as oxidizing agents. For example, see: (a) Barton, D. H. R.; Kitchin, J. P.; Lester, D. J.; Motherwell, W. B.; Papoula, M. T. B. Tetrahedron 1981, 37 (Supplement 1), 73-79. (b) Dodonov, V. A.; Gushchin, A. V.; Brilkina, T. G. J. Gen. Chem. USSR 1985, 55, 63-68; Zh. Obshch. Khim. 1985, 55, 73-80. Barton, D. H. R.; Yadav-Bhatnagar, N.; Finet, J.-P.; Khamsi, J.; Motherwell, W. B.; Stanforth, S. P. Tetrahedron 1987, 43, 323-332. Matano, Y.; Nomura, H. Angew. Chem., Int. Ed. 2002, 41, 3028-3031. (e) Komatsu, N. In Organobismuth Chemistry; Suzuki, H., Matano, Y. Eds.; Elsevier: New York, 2001; Chapter 5, pp 371-440. (f) Matano, Y. In Main Group Metals in Organic Synthesis; Yamamoto, H., Oshima, K., Eds.; Wiley-VCH: Weinheim, Germany, 2004; Chapter 14, pp 753-811, and references therein.
55. Pentavalent organobismuth compounds have been used as oxidizing agents. For example, see: (a) Barton, D. H. R.; Kitchin, J. P.; Lester, D. J.; Motherwell, W. B.; Papoula, M. T. B. Tetrahedron 1981, 37 (Supplement 1), 73-79. (b) Dodonov, V. A.; Gushchin, A. V.; Brilkina, T. G. J. Gen. Chem. USSR 1985, 55, 63-68; Zh. Obshch. Khim. 1985, 55, 73-80. Barton, D. H. R.; Yadav-Bhatnagar, N.; Finet, J.-P.; Khamsi, J.; Motherwell, W. B.; Stanforth, S. P. Tetrahedron 1987, 43, 323-332. Matano, Y.; Nomura, H. Angew. Chem., Int. Ed. 2002, 41, 3028-3031. (e) Komatsu, N. In Organobismuth Chemistry; Suzuki, H., Matano, Y. Eds.; Elsevier: New York, 2001; Chapter 5, pp 371-440. (f) Matano, Y. In Main Group Metals in Organic Synthesis; Yamamoto, H., Oshima, K., Eds.; Wiley-VCH: Weinheim, Germany, 2004; Chapter 14, pp 753-811, and references therein.
56. Pentavalent organobismuth compounds have been used as oxidizing agents. For example, see: (a) Barton, D. H. R.; Kitchin, J. P.; Lester, D. J.; Motherwell, W. B.; Papoula, M. T. B. Tetrahedron 1981, 37 (Supplement 1), 73-79. (b) Dodonov, V. A.; Gushchin, A. V.; Brilkina, T. G. J. Gen. Chem. USSR 1985, 55, 63-68; Zh. Obshch. Khim. 1985, 55, 73-80. Barton, D. H. R.; Yadav-Bhatnagar, N.; Finet, J.-P.; Khamsi, J.; Motherwell, W. B.; Stanforth, S. P. Tetrahedron 1987, 43, 323-332. Matano, Y.; Nomura, H. Angew. Chem., Int. Ed. 2002, 41, 3028-3031. (e) Komatsu, N. In Organobismuth Chemistry; Suzuki, H., Matano, Y. Eds.; Elsevier: New York, 2001; Chapter 5, pp 371-440. (f) Matano, Y. In Main Group Metals in Organic Synthesis; Yamamoto, H., Oshima, K., Eds.; Wiley-VCH: Weinheim, Germany, 2004; Chapter 14, pp 753-811, and references therein.
57. For preliminary results, see: Matano, Y.; Nomura, H. J. Am. Chem. Soc. 2001, 123, 6443-6444.
58. An attempt to prepare 3a using trist 2-methoxyphenyl)bismuthane and iodosylbenzene resulted in the formation of tetrakis(2methoxyphenyl)bismuthonium salts: Suzuki, H.; Ikegami, T.; Azuma, N. J. Chem. Soc., Perkin Trans. 1 1997, 1609-1616.
59. Irrespective of the degree of oligomerization and hydration, compounds 3 are represented as triarylbismuthane oxides throughout this paper.
60. The stibane oxide 5 was hydrated in the presence of water, and there was an equilibrium between the hydrate and the anhydride in solution. See the Experimental Section.
61. 2O (2.12(3), 2.02(3) Å): Hassan, A.; Breeze, S. R.; Courtenary, S.; Deslippe, C.; Wang, S. Organometallics 1996, 15, 5613-5621.
62. 2O (2.12(3), 2.02(3) Å): Hassan, A.; Breeze, S. R.; Courtenary, S.; Deslippe, C.; Wang, S. Organometallics 1996, 15, 5613-5621.
63. 2O (2.12(3), 2.02(3) Å): Hassan, A.; Breeze, S. R.; Courtenary, S.; Deslippe, C.; Wang, S. Organometallics 1996, 15, 5613-5621.
64. 2 (2.101(10), 2.073(9) A): Sasamori, T.; Arai, Y.; Takeda, M.; Okazaki, R.; Furukawa, Y.; Kimura, M.; Nagase, S.; Tokitoh, N. Bull. Chem. Soc. Jpn. 2002, 75, 661-675.
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67. 2 (2.280(4), 2.276(5) A): Rüther, R.; Huber, F.; Freut, H. Z. Anorg. Allg. Chem. 1986, 539, 110-126.
68. 2 (2.280(4), 2.276(5) A): Rüther, R.; Huber, F.; Freut, H. Z. Anorg. Allg. Chem. 1986, 539, 110-126.
69. 2 (2.280(4), 2.276(5) A): Rüther, R.; Huber, F.; Freut, H. Z. Anorg. Allg. Chem. 1986, 539, 110-126.
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71. 2O (1.958(13), 1.931(13) A; 1.943(13), 1.943(13) A): Ouchi, A.; Sato, S. Bull. Chem. Soc. Jpn. 1988, 61, 1806-1808.
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