Tail-to-Tail Dimerization of Acrylonitrile Catalyzed by Low-Valent Ruthenium Complexes

Bulletin of the Chemical Society of Japan

Volumn 71, Issue 6, 1998, Pages 1409-1415

  Fukuoka, Atsushi ^a,b   Nagano, Takeyuki ^a   Furuta, Shuichi ^a   Yoshizawa, Michito ^a   Hirano, Masafumi ^a   Komiya, Sanshiro ^a  

^a TOKYO UNIVERSITY OF AGRICULTURE AND TECHNOLOGY   (Japan)

^b HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0011558162     PISSN: 00092673     EISSN: None     Source Type: Journal    
DOI: 10.1246/bcsj.71.1409     Document Type: Article

References (64)

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33. By Ru complexes: a) R. J. McKinney and M. C. Colton, Organometallics, 5, 1080 (1986); b) C. Y. Ren, W. C. Cheng, W. C. Chan, C. H. Yeung, and C. P. Lau, J. Mol. Catal., 59, L1 (1990); c) R. Sustmann, H. J. Hornung, T. Schupp, and B. Patzke, J. Mol. Calal., 85, 149 (1993); d) P. Pertici, V. Ballantini, P. Salvadori, and M. A. Bennett, Organometallics, 14, 2565 (1995). By Rh complexes: e) T. Alderson, E. L. Jenner, and R. V. Lindsey, J. Am. Chem. Soc., 87, 5638 (1965); f) W. A. Nugent and R. J. McKinney, J. Mol. Catal., 29, 65 (1985); g) E. Hauptman, S. Sabo-Etienne, P. S. White, M. Brookhart, J. M. Garner, P. J. Fagan, and J. C. Calabrese, J. Am. Chem. Soc., 116, 8038 (1994), and references cited therein; h) Y. Kaneko, T. Kanke, S. Kiyooka, and K. Isobe, Chem. Lett., 1997, 23. By Pd complexes: i) M. G. Barlow, M. J. Bryant, R. N. Haszeldine, and A. G. Mackie, J. Organomet. Chem., 21, 215 (1970); j) G. Oehme and H. Pracejus, Tetrahedron Lett., 1979, 343; k) W. A. Nugent and F. W. Hobbs, J. Org. Chem., 48, 5364 (1983); l) P. Grenouilliet, D. Neibecker, and I. Tkatchenko, Organometallics, 3, 1130 (1984). By Ni complexes: m) G. Wilke, Angew. Chem., Int. Ed. Engl., 27, 185 (1988).
34. By Ru complexes: a) R. J. McKinney and M. C. Colton, Organometallics, 5, 1080 (1986); b) C. Y. Ren, W. C. Cheng, W. C. Chan, C. H. Yeung, and C. P. Lau, J. Mol. Catal., 59, L1 (1990); c) R. Sustmann, H. J. Hornung, T. Schupp, and B. Patzke, J. Mol. Calal., 85, 149 (1993); d) P. Pertici, V. Ballantini, P. Salvadori, and M. A. Bennett, Organometallics, 14, 2565 (1995). By Rh complexes: e) T. Alderson, E. L. Jenner, and R. V. Lindsey, J. Am. Chem. Soc., 87, 5638 (1965); f) W. A. Nugent and R. J. McKinney, J. Mol. Catal., 29, 65 (1985); g) E. Hauptman, S. Sabo-Etienne, P. S. White, M. Brookhart, J. M. Garner, P. J. Fagan, and J. C. Calabrese, J. Am. Chem. Soc., 116, 8038 (1994), and references cited therein; h) Y. Kaneko, T. Kanke, S. Kiyooka, and K. Isobe, Chem. Lett., 1997, 23. By Pd complexes: i) M. G. Barlow, M. J. Bryant, R. N. Haszeldine, and A. G. Mackie, J. Organomet. Chem., 21, 215 (1970); j) G. Oehme and H. Pracejus, Tetrahedron Lett., 1979, 343; k) W. A. Nugent and F. W. Hobbs, J. Org. Chem., 48, 5364 (1983); l) P. Grenouilliet, D. Neibecker, and I. Tkatchenko, Organometallics, 3, 1130 (1984). By Ni complexes: m) G. Wilke, Angew. Chem., Int. Ed. Engl., 27, 185 (1988).
35. By Ru complexes: a) R. J. McKinney and M. C. Colton, Organometallics, 5, 1080 (1986); b) C. Y. Ren, W. C. Cheng, W. C. Chan, C. H. Yeung, and C. P. Lau, J. Mol. Catal., 59, L1 (1990); c) R. Sustmann, H. J. Hornung, T. Schupp, and B. Patzke, J. Mol. Calal., 85, 149 (1993); d) P. Pertici, V. Ballantini, P. Salvadori, and M. A. Bennett, Organometallics, 14, 2565 (1995). By Rh complexes: e) T. Alderson, E. L. Jenner, and R. V. Lindsey, J. Am. Chem. Soc., 87, 5638 (1965); f) W. A. Nugent and R. J. McKinney, J. Mol. Catal., 29, 65 (1985); g) E. Hauptman, S. Sabo-Etienne, P. S. White, M. Brookhart, J. M. Garner, P. J. Fagan, and J. C. Calabrese, J. Am. Chem. Soc., 116, 8038 (1994), and references cited therein; h) Y. Kaneko, T. Kanke, S. Kiyooka, and K. Isobe, Chem. Lett., 1997, 23. By Pd complexes: i) M. G. Barlow, M. J. Bryant, R. N. Haszeldine, and A. G. Mackie, J. Organomet. Chem., 21, 215 (1970); j) G. Oehme and H. Pracejus, Tetrahedron Lett., 1979, 343; k) W. A. Nugent and F. W. Hobbs, J. Org. Chem., 48, 5364 (1983); l) P. Grenouilliet, D. Neibecker, and I. Tkatchenko, Organometallics, 3, 1130 (1984). By Ni complexes: m) G. Wilke, Angew. Chem., Int. Ed. Engl., 27, 185 (1988).
36. By Ru complexes: a) R. J. McKinney and M. C. Colton, Organometallics, 5, 1080 (1986); b) C. Y. Ren, W. C. Cheng, W. C. Chan, C. H. Yeung, and C. P. Lau, J. Mol. Catal., 59, L1 (1990); c) R. Sustmann, H. J. Hornung, T. Schupp, and B. Patzke, J. Mol. Calal., 85, 149 (1993); d) P. Pertici, V. Ballantini, P. Salvadori, and M. A. Bennett, Organometallics, 14, 2565 (1995). By Rh complexes: e) T. Alderson, E. L. Jenner, and R. V. Lindsey, J. Am. Chem. Soc., 87, 5638 (1965); f) W. A. Nugent and R. J. McKinney, J. Mol. Catal., 29, 65 (1985); g) E. Hauptman, S. Sabo-Etienne, P. S. White, M. Brookhart, J. M. Garner, P. J. Fagan, and J. C. Calabrese, J. Am. Chem. Soc., 116, 8038 (1994), and references cited therein; h) Y. Kaneko, T. Kanke, S. Kiyooka, and K. Isobe, Chem. Lett., 1997, 23. By Pd complexes: i) M. G. Barlow, M. J. Bryant, R. N. Haszeldine, and A. G. Mackie, J. Organomet. Chem., 21, 215 (1970); j) G. Oehme and H. Pracejus, Tetrahedron Lett., 1979, 343; k) W. A. Nugent and F. W. Hobbs, J. Org. Chem., 48, 5364 (1983); l) P. Grenouilliet, D. Neibecker, and I. Tkatchenko, Organometallics, 3, 1130 (1984). By Ni complexes: m) G. Wilke, Angew. Chem., Int. Ed. Engl., 27, 185 (1988).
37. By Ru complexes: a) R. J. McKinney and M. C. Colton, Organometallics, 5, 1080 (1986); b) C. Y. Ren, W. C. Cheng, W. C. Chan, C. H. Yeung, and C. P. Lau, J. Mol. Catal., 59, L1 (1990); c) R. Sustmann, H. J. Hornung, T. Schupp, and B. Patzke, J. Mol. Calal., 85, 149 (1993); d) P. Pertici, V. Ballantini, P. Salvadori, and M. A. Bennett, Organometallics, 14, 2565 (1995). By Rh complexes: e) T. Alderson, E. L. Jenner, and R. V. Lindsey, J. Am. Chem. Soc., 87, 5638 (1965); f) W. A. Nugent and R. J. McKinney, J. Mol. Catal., 29, 65 (1985); g) E. Hauptman, S. Sabo-Etienne, P. S. White, M. Brookhart, J. M. Garner, P. J. Fagan, and J. C. Calabrese, J. Am. Chem. Soc., 116, 8038 (1994), and references cited therein; h) Y. Kaneko, T. Kanke, S. Kiyooka, and K. Isobe, Chem. Lett., 1997, 23. By Pd complexes: i) M. G. Barlow, M. J. Bryant, R. N. Haszeldine, and A. G. Mackie, J. Organomet. Chem., 21, 215 (1970); j) G. Oehme and H. Pracejus, Tetrahedron Lett., 1979, 343; k) W. A. Nugent and F. W. Hobbs, J. Org. Chem., 48, 5364 (1983); l) P. Grenouilliet, D. Neibecker, and I. Tkatchenko, Organometallics, 3, 1130 (1984). By Ni complexes: m) G. Wilke, Angew. Chem., Int. Ed. Engl., 27, 185 (1988).
38. By Ru complexes: a) R. J. McKinney and M. C. Colton, Organometallics, 5, 1080 (1986); b) C. Y. Ren, W. C. Cheng, W. C. Chan, C. H. Yeung, and C. P. Lau, J. Mol. Catal., 59, L1 (1990); c) R. Sustmann, H. J. Hornung, T. Schupp, and B. Patzke, J. Mol. Calal., 85, 149 (1993); d) P. Pertici, V. Ballantini, P. Salvadori, and M. A. Bennett, Organometallics, 14, 2565 (1995). By Rh complexes: e) T. Alderson, E. L. Jenner, and R. V. Lindsey, J. Am. Chem. Soc., 87, 5638 (1965); f) W. A. Nugent and R. J. McKinney, J. Mol. Catal., 29, 65 (1985); g) E. Hauptman, S. Sabo-Etienne, P. S. White, M. Brookhart, J. M. Garner, P. J. Fagan, and J. C. Calabrese, J. Am. Chem. Soc., 116, 8038 (1994), and references cited therein; h) Y. Kaneko, T. Kanke, S. Kiyooka, and K. Isobe, Chem. Lett., 1997, 23. By Pd complexes: i) M. G. Barlow, M. J. Bryant, R. N. Haszeldine, and A. G. Mackie, J. Organomet. Chem., 21, 215 (1970); j) G. Oehme and H. Pracejus, Tetrahedron Lett., 1979, 343; k) W. A. Nugent and F. W. Hobbs, J. Org. Chem., 48, 5364 (1983); l) P. Grenouilliet, D. Neibecker, and I. Tkatchenko, Organometallics, 3, 1130 (1984). By Ni complexes: m) G. Wilke, Angew. Chem., Int. Ed. Engl., 27, 185 (1988).
39. By Ru complexes: a) R. J. McKinney and M. C. Colton, Organometallics, 5, 1080 (1986); b) C. Y. Ren, W. C. Cheng, W. C. Chan, C. H. Yeung, and C. P. Lau, J. Mol. Catal., 59, L1 (1990); c) R. Sustmann, H. J. Hornung, T. Schupp, and B. Patzke, J. Mol. Calal., 85, 149 (1993); d) P. Pertici, V. Ballantini, P. Salvadori, and M. A. Bennett, Organometallics, 14, 2565 (1995). By Rh complexes: e) T. Alderson, E. L. Jenner, and R. V. Lindsey, J. Am. Chem. Soc., 87, 5638 (1965); f) W. A. Nugent and R. J. McKinney, J. Mol. Catal., 29, 65 (1985); g) E. Hauptman, S. Sabo-Etienne, P. S. White, M. Brookhart, J. M. Garner, P. J. Fagan, and J. C. Calabrese, J. Am. Chem. Soc., 116, 8038 (1994), and references cited therein; h) Y. Kaneko, T. Kanke, S. Kiyooka, and K. Isobe, Chem. Lett., 1997, 23. By Pd complexes: i) M. G. Barlow, M. J. Bryant, R. N. Haszeldine, and A. G. Mackie, J. Organomet. Chem., 21, 215 (1970); j) G. Oehme and H. Pracejus, Tetrahedron Lett., 1979, 343; k) W. A. Nugent and F. W. Hobbs, J. Org. Chem., 48, 5364 (1983); l) P. Grenouilliet, D. Neibecker, and I. Tkatchenko, Organometallics, 3, 1130 (1984). By Ni complexes: m) G. Wilke, Angew. Chem., Int. Ed. Engl., 27, 185 (1988).
40. By Ru complexes: a) R. J. McKinney and M. C. Colton, Organometallics, 5, 1080 (1986); b) C. Y. Ren, W. C. Cheng, W. C. Chan, C. H. Yeung, and C. P. Lau, J. Mol. Catal., 59, L1 (1990); c) R. Sustmann, H. J. Hornung, T. Schupp, and B. Patzke, J. Mol. Calal., 85, 149 (1993); d) P. Pertici, V. Ballantini, P. Salvadori, and M. A. Bennett, Organometallics, 14, 2565 (1995). By Rh complexes: e) T. Alderson, E. L. Jenner, and R. V. Lindsey, J. Am. Chem. Soc., 87, 5638 (1965); f) W. A. Nugent and R. J. McKinney, J. Mol. Catal., 29, 65 (1985); g) E. Hauptman, S. Sabo-Etienne, P. S. White, M. Brookhart, J. M. Garner, P. J. Fagan, and J. C. Calabrese, J. Am. Chem. Soc., 116, 8038 (1994), and references cited therein; h) Y. Kaneko, T. Kanke, S. Kiyooka, and K. Isobe, Chem. Lett., 1997, 23. By Pd complexes: i) M. G. Barlow, M. J. Bryant, R. N. Haszeldine, and A. G. Mackie, J. Organomet. Chem., 21, 215 (1970); j) G. Oehme and H. Pracejus, Tetrahedron Lett., 1979, 343; k) W. A. Nugent and F. W. Hobbs, J. Org. Chem., 48, 5364 (1983); l) P. Grenouilliet, D. Neibecker, and I. Tkatchenko, Organometallics, 3, 1130 (1984). By Ni complexes: m) G. Wilke, Angew. Chem., Int. Ed. Engl., 27, 185 (1988).
41. By Ru complexes: a) R. J. McKinney and M. C. Colton, Organometallics, 5, 1080 (1986); b) C. Y. Ren, W. C. Cheng, W. C. Chan, C. H. Yeung, and C. P. Lau, J. Mol. Catal., 59, L1 (1990); c) R. Sustmann, H. J. Hornung, T. Schupp, and B. Patzke, J. Mol. Calal., 85, 149 (1993); d) P. Pertici, V. Ballantini, P. Salvadori, and M. A. Bennett, Organometallics, 14, 2565 (1995). By Rh complexes: e) T. Alderson, E. L. Jenner, and R. V. Lindsey, J. Am. Chem. Soc., 87, 5638 (1965); f) W. A. Nugent and R. J. McKinney, J. Mol. Catal., 29, 65 (1985); g) E. Hauptman, S. Sabo-Etienne, P. S. White, M. Brookhart, J. M. Garner, P. J. Fagan, and J. C. Calabrese, J. Am. Chem. Soc., 116, 8038 (1994), and references cited therein; h) Y. Kaneko, T. Kanke, S. Kiyooka, and K. Isobe, Chem. Lett., 1997, 23. By Pd complexes: i) M. G. Barlow, M. J. Bryant, R. N. Haszeldine, and A. G. Mackie, J. Organomet. Chem., 21, 215 (1970); j) G. Oehme and H. Pracejus, Tetrahedron Lett., 1979, 343; k) W. A. Nugent and F. W. Hobbs, J. Org. Chem., 48, 5364 (1983); l) P. Grenouilliet, D. Neibecker, and I. Tkatchenko, Organometallics, 3, 1130 (1984). By Ni complexes: m) G. Wilke, Angew. Chem., Int. Ed. Engl., 27, 185 (1988).
42. By Ru complexes: a) R. J. McKinney and M. C. Colton, Organometallics, 5, 1080 (1986); b) C. Y. Ren, W. C. Cheng, W. C. Chan, C. H. Yeung, and C. P. Lau, J. Mol. Catal., 59, L1 (1990); c) R. Sustmann, H. J. Hornung, T. Schupp, and B. Patzke, J. Mol. Calal., 85, 149 (1993); d) P. Pertici, V. Ballantini, P. Salvadori, and M. A. Bennett, Organometallics, 14, 2565 (1995). By Rh complexes: e) T. Alderson, E. L. Jenner, and R. V. Lindsey, J. Am. Chem. Soc., 87, 5638 (1965); f) W. A. Nugent and R. J. McKinney, J. Mol. Catal., 29, 65 (1985); g) E. Hauptman, S. Sabo-Etienne, P. S. White, M. Brookhart, J. M. Garner, P. J. Fagan, and J. C. Calabrese, J. Am. Chem. Soc., 116, 8038 (1994), and references cited therein; h) Y. Kaneko, T. Kanke, S. Kiyooka, and K. Isobe, Chem. Lett., 1997, 23. By Pd complexes: i) M. G. Barlow, M. J. Bryant, R. N. Haszeldine, and A. G. Mackie, J. Organomet. Chem., 21, 215 (1970); j) G. Oehme and H. Pracejus, Tetrahedron Lett., 1979, 343; k) W. A. Nugent and F. W. Hobbs, J. Org. Chem., 48, 5364 (1983); l) P. Grenouilliet, D. Neibecker, and I. Tkatchenko, Organometallics, 3, 1130 (1984). By Ni complexes: m) G. Wilke, Angew. Chem., Int. Ed. Engl., 27, 185 (1988).
43. By Ru complexes: a) R. J. McKinney and M. C. Colton, Organometallics, 5, 1080 (1986); b) C. Y. Ren, W. C. Cheng, W. C. Chan, C. H. Yeung, and C. P. Lau, J. Mol. Catal., 59, L1 (1990); c) R. Sustmann, H. J. Hornung, T. Schupp, and B. Patzke, J. Mol. Calal., 85, 149 (1993); d) P. Pertici, V. Ballantini, P. Salvadori, and M. A. Bennett, Organometallics, 14, 2565 (1995). By Rh complexes: e) T. Alderson, E. L. Jenner, and R. V. Lindsey, J. Am. Chem. Soc., 87, 5638 (1965); f) W. A. Nugent and R. J. McKinney, J. Mol. Catal., 29, 65 (1985); g) E. Hauptman, S. Sabo-Etienne, P. S. White, M. Brookhart, J. M. Garner, P. J. Fagan, and J. C. Calabrese, J. Am. Chem. Soc., 116, 8038 (1994), and references cited therein; h) Y. Kaneko, T. Kanke, S. Kiyooka, and K. Isobe, Chem. Lett., 1997, 23. By Pd complexes: i) M. G. Barlow, M. J. Bryant, R. N. Haszeldine, and A. G. Mackie, J. Organomet. Chem., 21, 215 (1970); j) G. Oehme and H. Pracejus, Tetrahedron Lett., 1979, 343; k) W. A. Nugent and F. W. Hobbs, J. Org. Chem., 48, 5364 (1983); l) P. Grenouilliet, D. Neibecker, and I. Tkatchenko, Organometallics, 3, 1130 (1984). By Ni complexes: m) G. Wilke, Angew. Chem., Int. Ed. Engl., 27, 185 (1988).
44. By Ru complexes: a) R. J. McKinney and M. C. Colton, Organometallics, 5, 1080 (1986); b) C. Y. Ren, W. C. Cheng, W. C. Chan, C. H. Yeung, and C. P. Lau, J. Mol. Catal., 59, L1 (1990); c) R. Sustmann, H. J. Hornung, T. Schupp, and B. Patzke, J. Mol. Calal., 85, 149 (1993); d) P. Pertici, V. Ballantini, P. Salvadori, and M. A. Bennett, Organometallics, 14, 2565 (1995). By Rh complexes: e) T. Alderson, E. L. Jenner, and R. V. Lindsey, J. Am. Chem. Soc., 87, 5638 (1965); f) W. A. Nugent and R. J. McKinney, J. Mol. Catal., 29, 65 (1985); g) E. Hauptman, S. Sabo-Etienne, P. S. White, M. Brookhart, J. M. Garner, P. J. Fagan, and J. C. Calabrese, J. Am. Chem. Soc., 116, 8038 (1994), and references cited therein; h) Y. Kaneko, T. Kanke, S. Kiyooka, and K. Isobe, Chem. Lett., 1997, 23. By Pd complexes: i) M. G. Barlow, M. J. Bryant, R. N. Haszeldine, and A. G. Mackie, J. Organomet. Chem., 21, 215 (1970); j) G. Oehme and H. Pracejus, Tetrahedron Lett., 1979, 343; k) W. A. Nugent and F. W. Hobbs, J. Org. Chem., 48, 5364 (1983); l) P. Grenouilliet, D. Neibecker, and I. Tkatchenko, Organometallics, 3, 1130 (1984). By Ni complexes: m) G. Wilke, Angew. Chem., Int. Ed. Engl., 27, 185 (1988).
45. By Ru complexes: a) R. J. McKinney and M. C. Colton, Organometallics, 5, 1080 (1986); b) C. Y. Ren, W. C. Cheng, W. C. Chan, C. H. Yeung, and C. P. Lau, J. Mol. Catal., 59, L1 (1990); c) R. Sustmann, H. J. Hornung, T. Schupp, and B. Patzke, J. Mol. Calal., 85, 149 (1993); d) P. Pertici, V. Ballantini, P. Salvadori, and M. A. Bennett, Organometallics, 14, 2565 (1995). By Rh complexes: e) T. Alderson, E. L. Jenner, and R. V. Lindsey, J. Am. Chem. Soc., 87, 5638 (1965); f) W. A. Nugent and R. J. McKinney, J. Mol. Catal., 29, 65 (1985); g) E. Hauptman, S. Sabo-Etienne, P. S. White, M. Brookhart, J. M. Garner, P. J. Fagan, and J. C. Calabrese, J. Am. Chem. Soc., 116, 8038 (1994), and references cited therein; h) Y. Kaneko, T. Kanke, S. Kiyooka, and K. Isobe, Chem. Lett., 1997, 23. By Pd complexes: i) M. G. Barlow, M. J. Bryant, R. N. Haszeldine, and A. G. Mackie, J. Organomet. Chem., 21, 215 (1970); j) G. Oehme and H. Pracejus, Tetrahedron Lett., 1979, 343; k) W. A. Nugent and F. W. Hobbs, J. Org. Chem., 48, 5364 (1983); l) P. Grenouilliet, D. Neibecker, and I. Tkatchenko, Organometallics, 3, 1130 (1984). By Ni complexes: m) G. Wilke, Angew. Chem., Int. Ed. Engl., 27, 185 (1988).
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