Nitrous oxide oxidation catalyzed by ruthenium porphyrin complex

Bulletin of the Chemical Society of Japan

Volumn 77, Issue 10, 2004, Pages 1905-1914

  Tanaka, Hirotaka ^a   Hashimoto, Kentaro ^a   Suzuki, Kyosuke ^a   Kitaichi, Yasunori ^a   Sato, Mitsuo ^a   Ikeno, Taketo ^a   Yamada, Tohru ^a  

^a KEIO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; ALCOHOLS; ALDEHYDES; CATALYSIS; COMPLEXATION; DERIVATIVES; HIGH TEMPERATURE EFFECTS; OXIDATION; PORPHYRINS; SULFURIC ACID;

OXIDANTS; REACTION CONDITIONS; RUTHENIUM PORPHYRIN;

NITROGEN OXIDES;

1 (TERT BUTYLDIMETHYLSILOXY) 2,3:6,7 DIEPOXY 3,7 DIMETHYL 2 OCTANE; 1 (TERT BUTYLDIMETHYLSILOXY) 6,7 EPOXY 3,7 DIMETHYL 2 OCTANE; 1 (TERT BUTYLDIMETHYLSILOXY) 6,7 EPOXY 3,7 DIMETHYL 2 OCTENE; 2 NONYL 1 OXASPIRO[2,5]OCTANE; 2,3 EPOXY 2 METHYLDODECENE; 2,3,7,8,12,13,17,18 OCTAETHYLPORPHYRIN; 5 (TERT BUTYLDIMETHYLSILOXYMETHYL) 2,3 EPOXYBICYCLO[2.2.1]HEPTANE; 5,10,15,20 TETRAKIS 2,6 DICHLOROPHENYLPORPHYRIN; 5,10,15,20 TETRAKIS 4 METHOXYPHENYLPORPHYRIN; 5,10,15,20 TETRAMESITYLPORPHYRIN; 5,10,15,20 TETRAPHENYLPORPHYRIN; 5,6 BETA EPOXYANDROSTERONE ACETATE; 5,6 BETA EPOXYCHOLESTERYL ACETATE; 5,6 BETA EPOXYCHOLESTERYL BROMIDE; 5,6 BETA EPOXYCHOLESTERYL DECANOATE; 5,6 BETA EPOXYCHOLESTERYL FORMATE; 5,6 BETA EPOXYPREGRENOLONE ACETATE; 5,6 EPOXYCHOLESTERYLETHYL CARBONATE; 6,7 EPOXY 3,7 DIMETHYL 2 OCTENYL ACETATE; ALCOHOL DERIVATIVE; ALDEHYDE DERIVATIVE; ALKENE DERIVATIVE; ANTHRACENE DERIVATIVE; BENZYL ALCOHOL DERIVATIVE; DIOXORUTHENIUM TETRAMESITYLPORPHYRIN; EPOXIDE; KETONE DERIVATIVE; NITROUS OXIDE; PORPHYRIN DERIVATIVE; RUTHENIUM COMPLEX; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; EPOXIDATION; HIGH TEMPERATURE; OXIDATION;

EID: 8444246399     PISSN: 00092673     EISSN: None     Source Type: Journal    
DOI: 10.1246/bcsj.77.1905     Document Type: Article

References (58)

1. Molecule of the year 1992: E. Culotta and D. E. Koshland, Jr., Science, 258, 1862 (1992).
2. 2O," Elsevier, New York (1985).
3. For example: a) W. C. Trogler, J. Chem. Educ., 72, 973 (1995). b) J. Fluckiger, A. Dallenbach, T. Blunier, B. Stauffer, T. F. Stocker, D. Raynaud, and J.-M. Barnola, Science, 285, 227 (1998). c) G. Centi, S. Perathoner, and F. Vazzana, CHEMTECH, 29, 48 (1999). d) M. A. K. Khalil, Annu. Rev. Energy Environ., 24, 645 (1999).
4. For example: a) W. C. Trogler, J. Chem. Educ., 72, 973 (1995). b) J. Fluckiger, A. Dallenbach, T. Blunier, B. Stauffer, T. F. Stocker, D. Raynaud, and J.-M. Barnola, Science, 285, 227 (1998). c) G. Centi, S. Perathoner, and F. Vazzana, CHEMTECH, 29, 48 (1999). d) M. A. K. Khalil, Annu. Rev. Energy Environ., 24, 645 (1999).
5. For example: a) W. C. Trogler, J. Chem. Educ., 72, 973 (1995). b) J. Fluckiger, A. Dallenbach, T. Blunier, B. Stauffer, T. F. Stocker, D. Raynaud, and J.-M. Barnola, Science, 285, 227 (1998). c) G. Centi, S. Perathoner, and F. Vazzana, CHEMTECH, 29, 48 (1999). d) M. A. K. Khalil, Annu. Rev. Energy Environ., 24, 645 (1999).
6. For example: a) W. C. Trogler, J. Chem. Educ., 72, 973 (1995). b) J. Fluckiger, A. Dallenbach, T. Blunier, B. Stauffer, T. F. Stocker, D. Raynaud, and J.-M. Barnola, Science, 285, 227 (1998). c) G. Centi, S. Perathoner, and F. Vazzana, CHEMTECH, 29, 48 (1999). d) M. A. K. Khalil, Annu. Rev. Energy Environ., 24, 645 (1999).
7. For example: a) W. Steinkopf and U. Kuhnel, Chem. Ber., 75, 1323 (1942). b) H. Suzuki, T. Murashima, I. Kozai, and T. Mori, J. Chem. Soc., Perkin Trans. 1, 1993, 1591. c) N. Nishiwaki, S. Sakaguchi, and Y. Ishii, J. Org. Chem., 67, 5663 (2002).
8. For example: a) W. Steinkopf and U. Kuhnel, Chem. Ber., 75, 1323 (1942). b) H. Suzuki, T. Murashima, I. Kozai, and T. Mori, J. Chem. Soc., Perkin Trans. 1, 1993, 1591. c) N. Nishiwaki, S. Sakaguchi, and Y. Ishii, J. Org. Chem., 67, 5663 (2002).
9. For example: a) W. Steinkopf and U. Kuhnel, Chem. Ber., 75, 1323 (1942). b) H. Suzuki, T. Murashima, I. Kozai, and T. Mori, J. Chem. Soc., Perkin Trans. 1, 1993, 1591. c) N. Nishiwaki, S. Sakaguchi, and Y. Ishii, J. Org. Chem., 67, 5663 (2002).
10. For example: a) T. Mukaiyama, E. Hata, and T. Yamada, Chem. Lett., 1995, 505. b) E. Hata, T. Yamada, and T. Mukaiyama, Bull. Chem. Soc. Jpn., 68, 3629 (1995). c) T. Itoh, Y. Matsuya, K. Nagata, and A. Osawa, Tetrahedron Lett., 37, 4165 (1996). d) J. A. Hrabie and L. K. Keefer, Chem. Rev., 102, 1135 (2002). e) T. Sugihara, K. Kuwahara, A. Wakabayashi, H. Takao, H. Imagawa, and M. Nishizawa, Chem. Commun., 2004, 216.
11. For example: a) T. Mukaiyama, E. Hata, and T. Yamada, Chem. Lett., 1995, 505. b) E. Hata, T. Yamada, and T. Mukaiyama, Bull. Chem. Soc. Jpn., 68, 3629 (1995). c) T. Itoh, Y. Matsuya, K. Nagata, and A. Osawa, Tetrahedron Lett., 37, 4165 (1996). d) J. A. Hrabie and L. K. Keefer, Chem. Rev., 102, 1135 (2002). e) T. Sugihara, K. Kuwahara, A. Wakabayashi, H. Takao, H. Imagawa, and M. Nishizawa, Chem. Commun., 2004, 216.
12. For example: a) T. Mukaiyama, E. Hata, and T. Yamada, Chem. Lett., 1995, 505. b) E. Hata, T. Yamada, and T. Mukaiyama, Bull. Chem. Soc. Jpn., 68, 3629 (1995). c) T. Itoh, Y. Matsuya, K. Nagata, and A. Osawa, Tetrahedron Lett., 37, 4165 (1996). d) J. A. Hrabie and L. K. Keefer, Chem. Rev., 102, 1135 (2002). e) T. Sugihara, K. Kuwahara, A. Wakabayashi, H. Takao, H. Imagawa, and M. Nishizawa, Chem. Commun., 2004, 216.
13. For example: a) T. Mukaiyama, E. Hata, and T. Yamada, Chem. Lett., 1995, 505. b) E. Hata, T. Yamada, and T. Mukaiyama, Bull. Chem. Soc. Jpn., 68, 3629 (1995). c) T. Itoh, Y. Matsuya, K. Nagata, and A. Osawa, Tetrahedron Lett., 37, 4165 (1996). d) J. A. Hrabie and L. K. Keefer, Chem. Rev., 102, 1135 (2002). e) T. Sugihara, K. Kuwahara, A. Wakabayashi, H. Takao, H. Imagawa, and M. Nishizawa, Chem. Commun., 2004, 216.
14. For example: a) T. Mukaiyama, E. Hata, and T. Yamada, Chem. Lett., 1995, 505. b) E. Hata, T. Yamada, and T. Mukaiyama, Bull. Chem. Soc. Jpn., 68, 3629 (1995). c) T. Itoh, Y. Matsuya, K. Nagata, and A. Osawa, Tetrahedron Lett., 37, 4165 (1996). d) J. A. Hrabie and L. K. Keefer, Chem. Rev., 102, 1135 (2002). e) T. Sugihara, K. Kuwahara, A. Wakabayashi, H. Takao, H. Imagawa, and M. Nishizawa, Chem. Commun., 2004, 216.
15. W. M. Graven, J. Am. Chem. Soc., 81, 6190 (1959).
16. For example: a) J. B. Brown, H. B. Henbest, and E. R. H. Jones, J. Chem. Soc., 1950, 3634. b) F. S. Bridson-Jones, G. D. Buckly, L. H. Cross, and A. P. Driver, J. Chem. Soc., 1951, 2999. c) S. Poh, R. Hernandez, M. Inagaki, and P. G. Jessop, Org. Lett., 1, 583 (1999). d) G. I. Panov, K. A. Dubkov, E. V. Starokon, and V. N. Parmon, React. Kinet. Catal. Lett., 76, 401 (2002).
17. For example: a) J. B. Brown, H. B. Henbest, and E. R. H. Jones, J. Chem. Soc., 1950, 3634. b) F. S. Bridson-Jones, G. D. Buckly, L. H. Cross, and A. P. Driver, J. Chem. Soc., 1951, 2999. c) S. Poh, R. Hernandez, M. Inagaki, and P. G. Jessop, Org. Lett., 1, 583 (1999). d) G. I. Panov, K. A. Dubkov, E. V. Starokon, and V. N. Parmon, React. Kinet. Catal. Lett., 76, 401 (2002).
18. For example: a) J. B. Brown, H. B. Henbest, and E. R. H. Jones, J. Chem. Soc., 1950, 3634. b) F. S. Bridson-Jones, G. D. Buckly, L. H. Cross, and A. P. Driver, J. Chem. Soc., 1951, 2999. c) S. Poh, R. Hernandez, M. Inagaki, and P. G. Jessop, Org. Lett., 1, 583 (1999). d) G. I. Panov, K. A. Dubkov, E. V. Starokon, and V. N. Parmon, React. Kinet. Catal. Lett., 76, 401 (2002).
19. For example: a) J. B. Brown, H. B. Henbest, and E. R. H. Jones, J. Chem. Soc., 1950, 3634. b) F. S. Bridson-Jones, G. D. Buckly, L. H. Cross, and A. P. Driver, J. Chem. Soc., 1951, 2999. c) S. Poh, R. Hernandez, M. Inagaki, and P. G. Jessop, Org. Lett., 1, 583 (1999). d) G. I. Panov, K. A. Dubkov, E. V. Starokon, and V. N. Parmon, React. Kinet. Catal. Lett., 76, 401 (2002).
20. For example: a) M. Iwamoto, J. Hirata, K. Matsukami, and S. Kagawa, J. Phys. Chem., 87, 903 (1983). b) E. Suzuki, K. Nakashiro, and Y. Ono, Chem. Lett., 1988, 953. c) G. I. Panov, G. A. Sheveleva, A. S. Kharitonov, V. N. Romannikov, and L. A. Vostrikova, Appl. Catal., 82, 31 (1992). d) G. I. Panov, A. S. Kharitonov, and V. I. Sobolev, Appl. Catal., 98, 1 (1993). e) L. V. Piryutko, A. S. Kharitonov, V. I. Bukhtiyarov, and G. I. Panov, Kinet. Catal., 38, 102 (1997). f) CHEMTECH, 27, 3 (1997).
21. For example: a) M. Iwamoto, J. Hirata, K. Matsukami, and S. Kagawa, J. Phys. Chem., 87, 903 (1983). b) E. Suzuki, K. Nakashiro, and Y. Ono, Chem. Lett., 1988, 953. c) G. I. Panov, G. A. Sheveleva, A. S. Kharitonov, V. N. Romannikov, and L. A. Vostrikova, Appl. Catal., 82, 31 (1992). d) G. I. Panov, A. S. Kharitonov, and V. I. Sobolev, Appl. Catal., 98, 1 (1993). e) L. V. Piryutko, A. S. Kharitonov, V. I. Bukhtiyarov, and G. I. Panov, Kinet. Catal., 38, 102 (1997). f) CHEMTECH, 27, 3 (1997).
22. For example: a) M. Iwamoto, J. Hirata, K. Matsukami, and S. Kagawa, J. Phys. Chem., 87, 903 (1983). b) E. Suzuki, K. Nakashiro, and Y. Ono, Chem. Lett., 1988, 953. c) G. I. Panov, G. A. Sheveleva, A. S. Kharitonov, V. N. Romannikov, and L. A. Vostrikova, Appl. Catal., 82, 31 (1992). d) G. I. Panov, A. S. Kharitonov, and V. I. Sobolev, Appl. Catal., 98, 1 (1993). e) L. V. Piryutko, A. S. Kharitonov, V. I. Bukhtiyarov, and G. I. Panov, Kinet. Catal., 38, 102 (1997). f) CHEMTECH, 27, 3 (1997).
23. For example: a) M. Iwamoto, J. Hirata, K. Matsukami, and S. Kagawa, J. Phys. Chem., 87, 903 (1983). b) E. Suzuki, K. Nakashiro, and Y. Ono, Chem. Lett., 1988, 953. c) G. I. Panov, G. A. Sheveleva, A. S. Kharitonov, V. N. Romannikov, and L. A. Vostrikova, Appl. Catal., 82, 31 (1992). d) G. I. Panov, A. S. Kharitonov, and V. I. Sobolev, Appl. Catal., 98, 1 (1993). e) L. V. Piryutko, A. S. Kharitonov, V. I. Bukhtiyarov, and G. I. Panov, Kinet. Catal., 38, 102 (1997). f) CHEMTECH, 27, 3 (1997).
24. For example: a) M. Iwamoto, J. Hirata, K. Matsukami, and S. Kagawa, J. Phys. Chem., 87, 903 (1983). b) E. Suzuki, K. Nakashiro, and Y. Ono, Chem. Lett., 1988, 953. c) G. I. Panov, G. A. Sheveleva, A. S. Kharitonov, V. N. Romannikov, and L. A. Vostrikova, Appl. Catal., 82, 31 (1992). d) G. I. Panov, A. S. Kharitonov, and V. I. Sobolev, Appl. Catal., 98, 1 (1993). e) L. V. Piryutko, A. S. Kharitonov, V. I. Bukhtiyarov, and G. I. Panov, Kinet. Catal., 38, 102 (1997). f) CHEMTECH, 27, 3 (1997).
25. For example: a) M. Iwamoto, J. Hirata, K. Matsukami, and S. Kagawa, J. Phys. Chem., 87, 903 (1983). b) E. Suzuki, K. Nakashiro, and Y. Ono, Chem. Lett., 1988, 953. c) G. I. Panov, G. A. Sheveleva, A. S. Kharitonov, V. N. Romannikov, and L. A. Vostrikova, Appl. Catal., 82, 31 (1992). d) G. I. Panov, A. S. Kharitonov, and V. I. Sobolev, Appl. Catal., 98, 1 (1993). e) L. V. Piryutko, A. S. Kharitonov, V. I. Bukhtiyarov, and G. I. Panov, Kinet. Catal., 38, 102 (1997). f) CHEMTECH, 27, 3 (1997).
26. Recent examples: a) R. Ben-Daniel, L. Eeiner, and R. Neumann, J. Am. Chem. Soc., 124, 8788 (2002). b) R. Ben-Daniel and R. Neumann, Angew. Chem., Int. Ed., 42, 92 (2003).
27. Recent examples: a) R. Ben-Daniel, L. Eeiner, and R. Neumann, J. Am. Chem. Soc., 124, 8788 (2002). b) R. Ben-Daniel and R. Neumann, Angew. Chem., Int. Ed., 42, 92 (2003).
28. a) S. G. Lias, J. E. Bartmess, J. L. Holmes, R. D. Levin, and W. G. Mallrd, J. Phys. Chem. Ref. Data, 17, Suppl. 1 (1988).
29. b) P. S. Drzaic, J. Marks, and J. I. Brauman, "Gas Phase Ion Chemistry," ed by M. T. Bowers, Academic Press (1984), Vol. 3, p. 167.
30. For example: a) F. Bottomley, D. E. Paez, and P. S. White, J. Am. Chem. Soc., 104, 5651 (1982). b) P. T. Matsunaga, J. C. Marropoulos, and G. L. Hillhouse, Polyhedron, 14, 175 (1990). c) G. A. Vaughan, P. B. Rupert, and G. L. Hillhouse, J. Am. Chem. Soc., 109, 5538 (1987). d) G. A. Vaughan, G. L. Hillhouse, and A. L. Rheingold, J. Am. Chem. Soc., 112, 7994 (1990).
31. For example: a) F. Bottomley, D. E. Paez, and P. S. White, J. Am. Chem. Soc., 104, 5651 (1982). b) P. T. Matsunaga, J. C. Marropoulos, and G. L. Hillhouse, Polyhedron, 14, 175 (1990). c) G. A. Vaughan, P. B. Rupert, and G. L. Hillhouse, J. Am. Chem. Soc., 109, 5538 (1987). d) G. A. Vaughan, G. L. Hillhouse, and A. L. Rheingold, J. Am. Chem. Soc., 112, 7994 (1990).
32. For example: a) F. Bottomley, D. E. Paez, and P. S. White, J. Am. Chem. Soc., 104, 5651 (1982). b) P. T. Matsunaga, J. C. Marropoulos, and G. L. Hillhouse, Polyhedron, 14, 175 (1990). c) G. A. Vaughan, P. B. Rupert, and G. L. Hillhouse, J. Am. Chem. Soc., 109, 5538 (1987). d) G. A. Vaughan, G. L. Hillhouse, and A. L. Rheingold, J. Am. Chem. Soc., 112, 7994 (1990).
33. For example: a) F. Bottomley, D. E. Paez, and P. S. White, J. Am. Chem. Soc., 104, 5651 (1982). b) P. T. Matsunaga, J. C. Marropoulos, and G. L. Hillhouse, Polyhedron, 14, 175 (1990). c) G. A. Vaughan, P. B. Rupert, and G. L. Hillhouse, J. Am. Chem. Soc., 109, 5538 (1987). d) G. A. Vaughan, G. L. Hillhouse, and A. L. Rheingold, J. Am. Chem. Soc., 112, 7994 (1990).
34. a) T. Yamada, K. Suzuki, K. Hashimoto, and T. Ikeno, Chem. Lett., 1999, 1043.
35. b) A. Yamamoto, S. Kitazume, L. S. Pu, and S. Ikeda, J. Am. Chem. Soc., 93, 371 (1971).
36. a) J. T. Groves and J. S. Roman, J. Am. Chem. Soc., 117, 5594 (1995).
37. b) J. T. Groves and R. Quinn, J. Am. Chem. Soc., 107, 5790 (1985).
38. J. T. Groves, K. Shalyaev, and J. Lee, "Oxometalloporphyrins in Oxidative Catalysis," in "Porphyrin Hand Book," ed by K. M. Kadish, K. M. Smith, and R. Guilard, Academic Press, New York (2000), Vol. 4, pp. 17-40.
39. a) G. A. Tolstikov, U. M. Dzhemilev, and V. P. Yurev, J. Org. Chem. U.S.S.R., 8, 2253 (1972).
40. b) P. Brougham, M. S. Cooper, D. A. Cummerson, H. Heaney, and N. Thompson, Synthesis, 1987, 1015.
41. c) J.-C. Marchon and R. Ramasseul, Synthesis, 1989, 389.
42. d) M. Taveres, R. Ramasseul, J.-C. Marchon, B. Bachet, C. Brassy, and J.-P. Mornon, J. Chem. Soc., Perkin Trans. 2, 1992, 1321.
43. 13b
44. The reaction in fluorobenzene generally gave better yields than benzene for the other substrates.
45. J. T. Groves, K.-H. Ahn, and R. Quinn, J. Am. Chem. Soc., 110, 4217 (1988).
46. The production of Ru(tmp)(CO) during the epoxidation with molecular oxygen was reported; B. Scharbert, E. Zeisberger, and E. Paulus, J. Organomet. Chem., 143, 493 (1995).
47. D. R. Boyd, N. D. Sharma, D. J. Stevenson, J. Chima, D. J. Gray, and H. Dalton, Tetrahedron Lett., 31, 3887 (1991).
48. K. Imagawa, T. Nagata, T. Yamada, and T. Mukaiyama, Chem. Lett., 1994, 527.
49. a) H. Ohtake, T. Higuchi, and M. Hirobe, J. Am. Chem. Soc., 114, 10660 (1992).
50. b) H. Ohtake, T. Higuchi, and M. Hirobe, Heterocydes, 40, 867 (1995).
51. S. Banfi, A. Maiocchi, A. Moggi, F. Montanari, and S. Quid, J. Chem. Soc., Chem. Commun., 1990, 1794.
52. E. J. Corey and A. Venkateswarlu, J. Am. Chem. Soc., 94, 6190 (1972).
53. K. C. Bass, Org. Synth., Coll. Vol., V, 398 (1973).
54. T. Yamada, K. Imagawa, and T. Mukaiyama, Chem. Lett., 1992, 2109.
55. M. Linskeseder and E. Zbiral, Liebigs Ann. Chem., 1978, 1076.
56. J. A. R. Salvador, M. L. Saemelo, and A. S. Camposneves, Tetrahedron Lett., 37, 687 (1996).
57. D. E. Over, M. Barded, J.-C. Marchon, and R. Ramasseul, Magn. Reson. Chem., 33, 224 (1995).
58. T. Takai, K. Hata, T. Yamada, and T. Mukaiyama, Bull. Chem. Soc. Jpn., 64, 2513 (1991).