Gif Chemistry: The present situation

Tetrahedron

Volumn 54, Issue 22, 1998, Pages 5805-5817

  Barton, Derek H R ^a  

^a TEXAS A AND M UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID; ADAMANTANE; CYCLOHEXANE; CYCLOHEXANECARBOXYLIC ACID DERIVATIVE; HYDROCARBON; HYDROGEN PEROXIDE; HYDROGEN SULFIDE; HYDROPEROXIDE DERIVATIVE; IRON; LIGAND; PICOLINIC ACID; PYRIDINE; RADICAL; SUPEROXIDE; TERT BUTYL HYDROPEROXIDE; ZINC;

CATALYSIS; CHEMISTRY; OXIDATION; PRIORITY JOURNAL; REACTION ANALYSIS; REVIEW;

EID: 0032575212     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00155-0     Document Type: Article

References (100)

1. 1. Barton, D.H.R.; Gastiger, M.J. and Motherwell, W.B. J. Chem. Soc. Chem. Commun. 1983, 41.
2. 2. Tabushi, I. and Yazaki, A. J. Am. Chem. Soc. 1981, 103, 7371.
3. 3. Barton, D.H.R.; Boivin, J.; Ozbalik, N. and Schwartzentruber, K.M. Tetrahedron Lett. 1985, 25, 4219, See also Powell, G.; Richens, D.T. and Khan, L. J. Chem. Res. (S) 1994, 506.
4. 3. Barton, D.H.R.; Boivin, J.; Ozbalik, N. and Schwartzentruber, K.M. Tetrahedron Lett. 1985, 25, 4219, See also Powell, G.; Richens, D.T. and Khan, L. J. Chem. Res. (S) 1994, 506.
5. 4. Barton, D.H.R.; Boivin, J.; Ozbalik, N. and Schwartzentruber, K.M. Tetrahedron Lett. 1985, 26, 447.
6. 5. Barton, D.H.R.; Halley, F.; Ozbalik, N.; Schmitt, M.; Young, E. and Balavoine, G. J.Am Chem. Soc. 1989, 111, 7144.
7. 6. Barton, D.H.R.; Beck, A.H. and Delanghe, N.C. Tetrahedron Lett. 1996, 37, 1555.
8. 7. Barton, D.H.R. and Delanghe, N.C. 1996, 37, 8137.
9. 8. Barton, D.H.R.; Boivin, J. and LeCoupanec, P. J. Chem. Soc. Chem. Commun. 1987, 1379. Balavoine, G.; Barton, D.H.R.; Boivin, J.; LeCoupanec, P. and Lelandais, P. New J. Chem., 1989, 13, 691. Barton, D.H.R. and Chabot, B. Tetrahedron 1996, 52, 10287.
10. 8. Barton, D.H.R.; Boivin, J. and LeCoupanec, P. J. Chem. Soc. Chem. Commun. 1987, 1379. Balavoine, G.; Barton, D.H.R.; Boivin, J.; LeCoupanec, P. and Lelandais, P. New J. Chem., 1989, 13, 691. Barton, D.H.R. and Chabot, B. Tetrahedron 1996, 52, 10287.
11. 8. Barton, D.H.R.; Boivin, J. and LeCoupanec, P. J. Chem. Soc. Chem. Commun. 1987, 1379. Balavoine, G.; Barton, D.H.R.; Boivin, J.; LeCoupanec, P. and Lelandais, P. New J. Chem., 1989, 13, 691. Barton, D.H.R. and Chabot, B. Tetrahedron 1996, 52, 10287.
12. 9. Barton, D.H.R.; Costas Salgueiro, M. and MacKinnon, J. Ibid. 1997, 53, 7417. Barton, D.H.R.; Li, T. and Peralez, E. J. Chem. Soc. Perkin 2 submitted for publication.
13. 9. Barton, D.H.R.; Costas Salgueiro, M. and MacKinnon, J. Ibid. 1997, 53, 7417. Barton, D.H.R.; Li, T. and Peralez, E. J. Chem. Soc. Perkin 2 submitted for publication.
14. 10. Barton, D.H.R. and Doller, D. Acc. Chem. Res. 1992, 25, 504. Dr. Dollar has recently applied Gif Chemistry to a study of potential drug metabolites. The major product of Gif oxidation was indeed simply related to the main metabolite of the specific drug (Doller, D.; Chackalamannil, S.; Stamford, A.; McKittrick, B and Czarniecki, M. Bioorg. Med. Chem. Lett. 1997, 7, 1381). It is much easier to carry out Gif chemistry than to isolate metabolites from natural sources. Often only minute amounts are available. We think that a routine application of Gif Chemistry would take little time and might shorten considerably the studies of drug metabolism.
15. 10. Barton, D.H.R. and Doller, D. Acc. Chem. Res. 1992, 25, 504. Dr. Dollar has recently applied Gif Chemistry to a study of potential drug metabolites. The major product of Gif oxidation was indeed simply related to the main metabolite of the specific drug (Doller, D.; Chackalamannil, S.; Stamford, A.; McKittrick, B and Czarniecki, M. Bioorg. Med. Chem. Lett. 1997, 7, 1381). It is much easier to carry out Gif chemistry than to isolate metabolites from natural sources. Often only minute amounts are available. We think that a routine application of Gif Chemistry would take little time and might shorten considerably the studies of drug metabolism.
16. 11. Balavoine, G.; Barton, D.H.R.; Boivin, J.; Gref, A.; Ozbalik, N. and Rivière, H. Tetrahedron Lett. 1986, 27, 2849. Idem, J. Chem. Soc. Chem. Commun. 1986, 1727. Balavoine, G.; Barton, D.H.R., Boivin, J.; Gref, A.; LeCoupanec, P.; Ozbalik, N.; Pestana, J.A.X. and Rivière, H. Tetrahedron 1988, 44, 1091. Balavoine, G.; Barton, D.H.R.; Boivin, J.; Gref, A.; Halley, I; Ozbalik, N.; Pestana, J.A.X. and Rivière, H. New J. Chem., 1990, 14, 175. Barton, D.H.R. and Sobkowiak, A. Ibid. 1996, 20, 929.
17. 11. Balavoine, G.; Barton, D.H.R.; Boivin, J.; Gref, A.; Ozbalik, N. and Rivière, H. Tetrahedron Lett. 1986, 27, 2849. Idem, J. Chem. Soc. Chem. Commun. 1986, 1727. Balavoine, G.; Barton, D.H.R., Boivin, J.; Gref, A.; LeCoupanec, P.; Ozbalik, N.; Pestana, J.A.X. and Rivière, H. Tetrahedron 1988, 44, 1091. Balavoine, G.; Barton, D.H.R.; Boivin, J.; Gref, A.; Halley, I; Ozbalik, N.; Pestana, J.A.X. and Rivière, H. New J. Chem., 1990, 14, 175. Barton, D.H.R. and Sobkowiak, A. Ibid. 1996, 20, 929.
18. 11. Balavoine, G.; Barton, D.H.R.; Boivin, J.; Gref, A.; Ozbalik, N. and Rivière, H. Tetrahedron Lett. 1986, 27, 2849. Idem, J. Chem. Soc. Chem. Commun. 1986, 1727. Balavoine, G.; Barton, D.H.R., Boivin, J.; Gref, A.; LeCoupanec, P.; Ozbalik, N.; Pestana, J.A.X. and Rivière, H. Tetrahedron 1988, 44, 1091. Balavoine, G.; Barton, D.H.R.; Boivin, J.; Gref, A.; Halley, I; Ozbalik, N.; Pestana, J.A.X. and Rivière, H. New J. Chem., 1990, 14, 175. Barton, D.H.R. and Sobkowiak, A. Ibid. 1996, 20, 929.
19. 11. Balavoine, G.; Barton, D.H.R.; Boivin, J.; Gref, A.; Ozbalik, N. and Rivière, H. Tetrahedron Lett. 1986, 27, 2849. Idem, J. Chem. Soc. Chem. Commun. 1986, 1727. Balavoine, G.; Barton, D.H.R., Boivin, J.; Gref, A.; LeCoupanec, P.; Ozbalik, N.; Pestana, J.A.X. and Rivière, H. Tetrahedron 1988, 44, 1091. Balavoine, G.; Barton, D.H.R.; Boivin, J.; Gref, A.; Halley, I; Ozbalik, N.; Pestana, J.A.X. and Rivière, H. New J. Chem., 1990, 14, 175. Barton, D.H.R. and Sobkowiak, A. Ibid. 1996, 20, 929.
20. 11. Balavoine, G.; Barton, D.H.R.; Boivin, J.; Gref, A.; Ozbalik, N. and Rivière, H. Tetrahedron Lett. 1986, 27, 2849. Idem, J. Chem. Soc. Chem. Commun. 1986, 1727. Balavoine, G.; Barton, D.H.R., Boivin, J.; Gref, A.; LeCoupanec, P.; Ozbalik, N.; Pestana, J.A.X. and Rivière, H. Tetrahedron 1988, 44, 1091. Balavoine, G.; Barton, D.H.R.; Boivin, J.; Gref, A.; Halley, I; Ozbalik, N.; Pestana, J.A.X. and Rivière, H. New J. Chem., 1990, 14, 175. Barton, D.H.R. and Sobkowiak, A. Ibid. 1996, 20, 929.
21. 12. Perkins, M.J. Chem. Soc. Rev. 1996, 25, 229.
22. 13. Barton D.H.R. and Launay, F. Tetrahedron 1997, 53, 14565.
23. (b) See, for example, Robinson, C.H.; Gnoj, O.; Mitchell, A.; Oliveto, E.P. and Barton, D.H.R. Tetrahedron 1965, 21, 743.
24. 14. Barton, D.H.R.; Hay-Motherwell, R.S. and Motherwell, W.B. Tetrahedron Lett. 1983, 24, 1979.
25. 15. Balavoine, G.; Barton, D.H.R.; Boivin, G. and Gref, A. Ibid. 1990, 31, 659.
26. 16. About-Jaudet, E.; Barton, D.H.R.; Csuhai, E. and Ozbalik, N. Ibid. 1990, 31, 1657.
27. 17. Barton, D.H.R. and Chavasiri, W. Tetrahedron 1997, 53, 2997.
28. 2 with and without picolinic acid. For cis-decalin the normalised ratio of secondary to tertiary oxidation was 1.8 and 2.4. For trans-decalin the ratios were 2.3 and 3.5.
29. 19. Gastiger, M. Ph.D. Thesis, Université de Paris-Sud, Orsay, France, 1984.
30. 20. Barton, D.H.R.; Hu, B; Taylor, D.K. and Rojas Wahl, R.V. J. Chem. Soc. Perkin Trans. 2 1996, 1031.
31. 21. Barton, D.H.R; Bévière, S.D.; Chavasiri, W.; Csuhai, E.; Doller, D. and Liu W.-G. J. Am. Chem. Soc. 1992, 114, 2147.
32. 22. Barton, D.H.R., Bévière, S.D. and Doller, D. Tetrahedron Lett. 1991, 32, 4671.
33. 23. Balavoine, G.; Barton, D.H.R.; Gref, A. and Lellouche, I. Tetrahedron Lett. 1991, 32, 2351.
34. 24. Balavoine, G.; Barton, D.H.R.; Gref, A. and Lellouche, I. Tetrahedron 1992, 48, 1883.
35. 25. Barton, D.H.R.; Lalic, G. and Smith, J.A. Tetrahedron 1998, in press. For other applications of tributylphosphine in selenium chemistry see Grieco, P.A.; Jaw, J.Y.; Claremon, D.A. and Nicolaou, K.C. J. Org. Chem. 1981, 46 1215.
36. 25. Barton, D.H.R.; Lalic, G. and Smith, J.A. Tetrahedron 1998, in press. For other applications of tributylphosphine in selenium chemistry see Grieco, P.A.; Jaw, J.Y.; Claremon, D.A. and Nicolaou, K.C. J. Org. Chem. 1981, 46 1215.
37. 26. Barton, D.H.R. and Bévière, S.D. Tetrahedron Lett. 1993, 34, 5689.
38. 27. Barton, D.H.R. and Wang, T.-L. Tetrahedron 1994, 50, 1011. Barton, D.H.R. and Chavasiri, W. Tetrahedron 1994, 50, 19. Barton, D.H.R. and Chavasiri, W. Tetrahedron 1994, 50, 47. Barton, D.H.R. and Wang, T.-L. Tetrahedron Lett. 1994, 35, 1519.
39. 27. Barton, D.H.R. and Wang, T.-L. Tetrahedron 1994, 50, 1011. Barton, D.H.R. and Chavasiri, W. Tetrahedron 1994, 50, 19. Barton, D.H.R. and Chavasiri, W. Tetrahedron 1994, 50, 47. Barton, D.H.R. and Wang, T.-L. Tetrahedron Lett. 1994, 35, 1519.
40. 27. Barton, D.H.R. and Wang, T.-L. Tetrahedron 1994, 50, 1011. Barton, D.H.R. and Chavasiri, W. Tetrahedron 1994, 50, 19. Barton, D.H.R. and Chavasiri, W. Tetrahedron 1994, 50, 47. Barton, D.H.R. and Wang, T.-L. Tetrahedron Lett. 1994, 35, 1519.
41. 27. Barton, D.H.R. and Wang, T.-L. Tetrahedron 1994, 50, 1011. Barton, D.H.R. and Chavasiri, W. Tetrahedron 1994, 50, 19. Barton, D.H.R. and Chavasiri, W. Tetrahedron 1994, 50, 47. Barton, D.H.R. and Wang, T.-L. Tetrahedron Lett. 1994, 35, 1519.
42. 28. Minisci, F. and Fontana, F. Tetrahedron Lett. 1994, 35, 1427.
43. 29. Kochi, J.K. in Free Radicals, Kochi, J.K Ed.; John Wiley and Sons Inc., New York, 1973.
44. 30. Clark, L.J. Anal. Chim. 1962, 34, 348.
45. 31. Minisci, F.; Fontana, F.; Araneo, S.; Recupero, F.; Zhao, L. Synlett 1996, 119.
46. 2-O-OH. The alkoxy radical derived from the latter fragments rapidly to give benzyl radicals. We agree that the chemistry studied is radical chemistry based on monosubstituted hydroperoxide fragmentation to alkoxy radicals. It is not part of Gif Chemistry at all.
47. 2-O-OH. The alkoxy radical derived from the latter fragments rapidly to give benzyl radicals. We agree that the chemistry studied is radical chemistry based on monosubstituted hydroperoxide fragmentation to alkoxy radicals. It is not part of Gif Chemistry at all.
48. 33. Barton, D.H.R. Synlett, 1997, 229. Barton, D.H.R.; LeGloahec, V.N.; Patin, H. and (in part) Launay, F. New J. Chem. in press. Barton, D.H.R.; LeGloahec, V.N. and Patin, H. Ibid. in press.
49. 33. Barton, D.H.R. Synlett, 1997, 229. Barton, D.H.R.; LeGloahec, V.N.; Patin, H. and (in part) Launay, F. New J. Chem. in press. Barton, D.H.R.; LeGloahec, V.N. and Patin, H. Ibid. in press.
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52. 34. Barton D.H.R.; Launay, F.; LeGloahec, V.N.; Li, T. and Smith, F. Tetrahedron Lett. 1997, 38, 8491. Barton, D.H.R. and LeGloahec, V.N. Tetrahedron Lett. submitted for publication.
53. 35. Hage, J.P.; Llobet, A. and Sawyer, D.T. Bioorg. and Med. Chem. 1995, 3, 1383. Kang, C.; Redman, C.; Cepak, V. and Sawyer, D.T. Ibid., 1993, 1, 125.
54. 35. Hage, J.P.; Llobet, A. and Sawyer, D.T. Bioorg. and Med. Chem. 1995, 3, 1383. Kang, C.; Redman, C.; Cepak, V. and Sawyer, D.T. Ibid., 1993, 1, 125.
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57. 37. Bardin, C.; Barton, D.H.R.; Hu, B.; Rojas Wahl, R.U. and Taylor, D.K. Tetrahedron Lett. 1994, 35, 5805. Barton, D.H.R.; Chabot, B.M.; Delanghe, N.C.; Hu, B.; LeGloahec, V.N. and Rojas Wahl, R.V. Ibid. 1995, 36, 7007.
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59. 39. Barton, D.H.R.; Hu, B.; Li, T. and Mackinnon, J. Tetrahedron Lett. 1996, 37, 8329.
60. 40. Barton, D.H.R. and Hu, B. Tetrahedron 1996, 52, 10313.
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66. 43. Newcomb, M. and Marek, M.B. J. Am. Chem. Soc. 1990, 112, 9662. Newcomb, M. Tetrahedron 1993, 49, 7417.
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68. 45. Ingold, K.U. Aldrichchimica Acta 1989, 22, 69.
69. 46. Barton, D.H.R. and Li, T. J. Chem. Soc. Chem. Commun. in press.
70. 47. Schuchardt, U.; Krähembül, C.E.Z. and Carvalho, W.A. New J. Chem. 1991, 15, 955. Schuchardt, U.; Carvalho, W.A. and Spinacé, E.V. Synlett 1993, 713. The latter article makes reference to all prior work by Prof. Schuchardt.
71. 47. Schuchardt, U.; Krähembül, C.E.Z. and Carvalho, W.A. New J. Chem. 1991, 15, 955. Schuchardt, U.; Carvalho, W.A. and Spinacé, E.V. Synlett 1993, 713. The latter article makes reference to all prior work by Prof. Schuchardt.
72. 48. Sugimoto, H. and Sawyer, D.T. J. Am. Chem. Soc. 1984, 106, 4283. Idem, Ibid. 1985, 107, 5712.
73. 48. Sugimoto, H. and Sawyer, D.T. J. Am. Chem. Soc. 1984, 106, 4283. Idem, Ibid. 1985, 107, 5712.
74. 49. Sheu, C.; Sobkowiak, A.; Zhang, L.; Ozbalik, N.; Barton, D.H.R. and Sawyer, D.T. Ibid. 1989, 111, 8030.
75. 50. Sheu, C., Robert, S.A.; Cofré, P.; Ross Jr., B.; Sobkowiak, A.; Sawyer, D.T. and Kanofsky, J.R. Ibid. 1990, 112, 1936. Sheu, C.; Sobkowiak, A.; Jeon, S. and Sawyer, D.T. Ibid. 1990, 112, 879. Sheu, C. and Sawyer, D.T. Ibid. 1990, 112, 8212. Tung, H.-C.; Kaug, C. and Sawyer, D.T. Ibid. 1992, 114, 3445.
76. 50. Sheu, C., Robert, S.A.; Cofré, P.; Ross Jr., B.; Sobkowiak, A.; Sawyer, D.T. and Kanofsky, J.R. Ibid. 1990, 112, 1936. Sheu, C.; Sobkowiak, A.; Jeon, S. and Sawyer, D.T. Ibid. 1990, 112, 879. Sheu, C. and Sawyer, D.T. Ibid. 1990, 112, 8212. Tung, H.-C.; Kaug, C. and Sawyer, D.T. Ibid. 1992, 114, 3445.
77. 50. Sheu, C., Robert, S.A.; Cofré, P.; Ross Jr., B.; Sobkowiak, A.; Sawyer, D.T. and Kanofsky, J.R. Ibid. 1990, 112, 1936. Sheu, C.; Sobkowiak, A.; Jeon, S. and Sawyer, D.T. Ibid. 1990, 112, 879. Sheu, C. and Sawyer, D.T. Ibid. 1990, 112, 8212. Tung, H.-C.; Kaug, C. and Sawyer, D.T. Ibid. 1992, 114, 3445.
78. 50. Sheu, C., Robert, S.A.; Cofré, P.; Ross Jr., B.; Sobkowiak, A.; Sawyer, D.T. and Kanofsky, J.R. Ibid. 1990, 112, 1936. Sheu, C.; Sobkowiak, A.; Jeon, S. and Sawyer, D.T. Ibid. 1990, 112, 879. Sheu, C. and Sawyer, D.T. Ibid. 1990, 112, 8212. Tung, H.-C.; Kaug, C. and Sawyer, D.T. Ibid. 1992, 114, 3445.
79. 51. Singh, B.; Long, J.R.; Fabrizi de Biani, F.; Gatteschi, D. and Stavropoulos, P. J. Am. Chem. Soc. 1997, 119, 7030. Singh, B.; Long, J.R.; Papaefthymiou, G.C. and Stavropoulos, P. J. Am. Chem. Soc. 1996, 118, 5824.
80. 51. Singh, B.; Long, J.R.; Fabrizi de Biani, F.; Gatteschi, D. and Stavropoulos, P. J. Am. Chem. Soc. 1997, 119, 7030. Singh, B.; Long, J.R.; Papaefthymiou, G.C. and Stavropoulos, P. J. Am. Chem. Soc. 1996, 118, 5824.
81. 52. Kim, S.-B.; Lee, K.-W.; Kim, Y.-J. and Hong, S.I. Bull. Korean Chem. Soc. 1994, 15 424.
82. 53. Kim, S.-B. and Lee, K.-W. Korean J. Chem. Eng. 1995, 12, 188.
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85. 55. Jun, K.-W.; Lee, K.-W.; Shim, E.-K. and Cho, N.-S. Applied Catalysis A. Gen. 1993, 96, 269. Jun, K.-W.; Shim, E.-K.; Park, S.-E. and Lee, K.-W. Bull. Korean Chem. Soc, 1995, 16, 398. Kim, S.-B.; Jun, K.-W.; Kin, S-Bo. and Lee, K.-W. Chem. Lett. 1995, 535.
86. 55. Jun, K.-W.; Lee, K.-W.; Shim, E.-K. and Cho, N.-S. Applied Catalysis A. Gen. 1993, 96, 269. Jun, K.-W.; Shim, E.-K.; Park, S.-E. and Lee, K.-W. Bull. Korean Chem. Soc, 1995, 16, 398. Kim, S.-B.; Jun, K.-W.; Kin, S-Bo. and Lee, K.-W. Chem. Lett. 1995, 535.
87. 56. Barton, D.H.R. Ibid. 1996, 237. See also Synlett 1997, 229.
88. 56. Barton, D.H.R. Ibid. 1996, 237. See also Synlett 1997, 229.
89. 57. Knight, C. and Perkins, M.J. J. Chem. Soc. Chem. Commun. 1991, 925.
90. 58. Barton, D.H.R.; Csuhai, E.; Doller, D.; Ozbalik, N. and Senglet, N. Tetrahedron Lett. 1990, 31, 3097. Barton, D.H.R.; Csuhai, E. and Doller, D. Tetrahedron Lett. 1992, 33, 3413. Barton, D.H.R.; Csuhai, E. and Doller, D. Tetrahedron 1992, 48, 9195.
91. 58. Barton, D.H.R.; Csuhai, E.; Doller, D.; Ozbalik, N. and Senglet, N. Tetrahedron Lett. 1990, 31, 3097. Barton, D.H.R.; Csuhai, E. and Doller, D. Tetrahedron Lett. 1992, 33, 3413. Barton, D.H.R.; Csuhai, E. and Doller, D. Tetrahedron 1992, 48, 9195.
92. 58. Barton, D.H.R.; Csuhai, E.; Doller, D.; Ozbalik, N. and Senglet, N. Tetrahedron Lett. 1990, 31, 3097. Barton, D.H.R.; Csuhai, E. and Doller, D. Tetrahedron Lett. 1992, 33, 3413. Barton, D.H.R.; Csuhai, E. and Doller, D. Tetrahedron 1992, 48, 9195.
93. 59. Barton, D.H.R. Csuhai, E. and Doller, D. Tetrahedron Lett. 1992, 33, 3413. Idem, Tetrahedron 1992, 48, 9195.
94. 59. Barton, D.H.R. Csuhai, E. and Doller, D. Tetrahedron Lett. 1992, 33, 3413. Idem, Tetrahedron 1992, 48, 9195.
95. 60. Barton, D.H.R.; Csuhai, E. and Ozbalik, N. Tetrahedron 1990, 46, 3743.
96. 61. Barton, D.H.R.; Chabot, B.M. and Hu, B. Tetrahedron Lett. 1996, 37, 1755.
97. 62. Barton, D.H.R.; Chabot, B.M. and Hu, B. Tetrahedron 1996, 52, 10301.
98. 63. Barton, D.H.R. and Delanghe, N.C. Tetrahedron submitted for publication.
99. 64. Barton, D.H.R.; Boivin, J. and LeCoupanec, P. J. Chem. Soc., Chem. Commun. 1987, 1379. Balavoine, G.; Barton, D.H.R.; Boivin, J.; LeCoupanec, P. and Lelandais, P. New J. Chem. 1989, 13, 691.
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