The functionalization of saturated hydrocarbons. Part 34. A study on the mechanism of tempo trapping in GIF-type systems

Tetrahedron

Volumn 52, Issue 31, 1996, Pages 10301-10312

  Barton, Derek H R ^a   Chabot, Béatrice M ^a   Hu, Bin ^a  

^a TEXAS A AND M UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PIPERIDINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; PHOTOLYSIS; PRIORITY JOURNAL; REACTION ANALYSIS; SPIN LABELING; TECHNIQUE;

EID: 0030605919     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00565-0     Document Type: Article

References (37)

1. 1 Olah, G. A.; Molnar, A. Hydrocarbon Chemistry Wiley & Sons: New York, Chichester, 1995.
2. 2 Barton, D. H. R.; Sawyer, D. T.; Martel, A. E., Eds. The Activation Of Dioxygen and Homogeneous Catalytic Oxidation Plenum Press: New York, London, 1993.
3. 3 Barton, D. H. R.; Gastiger, M. J.; Motherwell, W. B. J. Chem. Soc., Chem. Commun. 1983, 41-43.; Barton, D. H. R.; Doller, D. Acc. Chem. Res. 1992, 25, 504-512.
4. 3 Barton, D. H. R.; Gastiger, M. J.; Motherwell, W. B. J. Chem. Soc., Chem. Commun. 1983, 41-43.; Barton, D. H. R.; Doller, D. Acc. Chem. Res. 1992, 25, 504-512.
5. 4 For other significant contributions to Gif chemistry see: Cofré, P.; Richert, S. A.; Sobkowiak, A.; Sawyer, D. T. Inorg. Chem. 1990, 29, 2645-2651.; Tung, H.C.; Kang, C.; Sawyer, D. T. J. Am. Chem. Soc. 1992, 114, 3445-3455 and references cited therein. Schuchardt, U.; Krähembühl, E. Z.,; Carvalho, W. A.; New J. Chem. 1991, 15, 955-958. Schuchardt, U.; Carvalho, W. A.; Spinacé, E. V. Synlett 1993, 713-718 and references there cited. Powell, G.; Richens, D. T.; Khan, L. J. Chem. Research(s). 1994,506-507. Briffaud, T.; Larpent, C.; Patin, H. J. Chem. Soc.Chem.Commun. 1990, 1193-1194. Kim, S.B.; Lee, K.W.; Kim, Y. J.; Hong, S. I. Bull. Korean Chem. Soc. 1994, 15, 424-427. Lee, K.-W.; Kim, S. B.; Jun, K.W.; Shim, E. K. New. J. Chem., 1993, 17, 409-411 and references there cited..
6. 4 For other significant contributions to Gif chemistry see: Cofré, P.; Richert, S. A.; Sobkowiak, A.; Sawyer, D. T. Inorg. Chem. 1990, 29, 2645-2651.; Tung, H.C.; Kang, C.; Sawyer, D. T. J. Am. Chem. Soc. 1992, 114, 3445-3455 and references cited therein. Schuchardt, U.; Krähembühl, E. Z.,; Carvalho, W. A.; New J. Chem. 1991, 15, 955-958. Schuchardt, U.; Carvalho, W. A.; Spinacé, E. V. Synlett 1993, 713-718 and references there cited. Powell, G.; Richens, D. T.; Khan, L. J. Chem. Research(s). 1994,506-507. Briffaud, T.; Larpent, C.; Patin, H. J. Chem. Soc.Chem.Commun. 1990, 1193-1194. Kim, S.B.; Lee, K.W.; Kim, Y. J.; Hong, S. I. Bull. Korean Chem. Soc. 1994, 15, 424-427. Lee, K.-W.; Kim, S. B.; Jun, K.W.; Shim, E. K. New. J. Chem., 1993, 17, 409-411 and references there cited..
7. 4 For other significant contributions to Gif chemistry see: Cofré, P.; Richert, S. A.; Sobkowiak, A.; Sawyer, D. T. Inorg. Chem. 1990, 29, 2645-2651.; Tung, H.C.; Kang, C.; Sawyer, D. T. J. Am. Chem. Soc. 1992, 114, 3445-3455 and references cited therein. Schuchardt, U.; Krähembühl, E. Z.,; Carvalho, W. A.; New J. Chem. 1991, 15, 955-958. Schuchardt, U.; Carvalho, W. A.; Spinacé, E. V. Synlett 1993, 713-718 and references there cited. Powell, G.; Richens, D. T.; Khan, L. J. Chem. Research(s). 1994,506-507. Briffaud, T.; Larpent, C.; Patin, H. J. Chem. Soc.Chem.Commun. 1990, 1193-1194. Kim, S.B.; Lee, K.W.; Kim, Y. J.; Hong, S. I. Bull. Korean Chem. Soc. 1994, 15, 424-427. Lee, K.-W.; Kim, S. B.; Jun, K.W.; Shim, E. K. New. J. Chem., 1993, 17, 409-411 and references there cited..
8. 4 For other significant contributions to Gif chemistry see: Cofré, P.; Richert, S. A.; Sobkowiak, A.; Sawyer, D. T. Inorg. Chem. 1990, 29, 2645-2651.; Tung, H.C.; Kang, C.; Sawyer, D. T. J. Am. Chem. Soc. 1992, 114, 3445-3455 and references cited therein. Schuchardt, U.; Krähembühl, E. Z.,; Carvalho, W. A.; New J. Chem. 1991, 15, 955-958. Schuchardt, U.; Carvalho, W. A.; Spinacé, E. V. Synlett 1993, 713-718 and references there cited. Powell, G.; Richens, D. T.; Khan, L. J. Chem. Research(s). 1994,506-507. Briffaud, T.; Larpent, C.; Patin, H. J. Chem. Soc.Chem.Commun. 1990, 1193-1194. Kim, S.B.; Lee, K.W.; Kim, Y. J.; Hong, S. I. Bull. Korean Chem. Soc. 1994, 15, 424-427. Lee, K.-W.; Kim, S. B.; Jun, K.W.; Shim, E. K. New. J. Chem., 1993, 17, 409-411 and references there cited..
9. 4 For other significant contributions to Gif chemistry see: Cofré, P.; Richert, S. A.; Sobkowiak, A.; Sawyer, D. T. Inorg. Chem. 1990, 29, 2645-2651.; Tung, H.C.; Kang, C.; Sawyer, D. T. J. Am. Chem. Soc. 1992, 114, 3445-3455 and references cited therein. Schuchardt, U.; Krähembühl, E. Z.,; Carvalho, W. A.; New J. Chem. 1991, 15, 955-958. Schuchardt, U.; Carvalho, W. A.; Spinacé, E. V. Synlett 1993, 713-718 and references there cited. Powell, G.; Richens, D. T.; Khan, L. J. Chem. Research(s). 1994,506-507. Briffaud, T.; Larpent, C.; Patin, H. J. Chem. Soc.Chem.Commun. 1990, 1193-1194. Kim, S.B.; Lee, K.W.; Kim, Y. J.; Hong, S. I. Bull. Korean Chem. Soc. 1994, 15, 424-427. Lee, K.-W.; Kim, S. B.; Jun, K.W.; Shim, E. K. New. J. Chem., 1993, 17, 409-411 and references there cited..
10. 4 For other significant contributions to Gif chemistry see: Cofré, P.; Richert, S. A.; Sobkowiak, A.; Sawyer, D. T. Inorg. Chem. 1990, 29, 2645-2651.; Tung, H.C.; Kang, C.; Sawyer, D. T. J. Am. Chem. Soc. 1992, 114, 3445-3455 and references cited therein. Schuchardt, U.; Krähembühl, E. Z.,; Carvalho, W. A.; New J. Chem. 1991, 15, 955-958. Schuchardt, U.; Carvalho, W. A.; Spinacé, E. V. Synlett 1993, 713-718 and references there cited. Powell, G.; Richens, D. T.; Khan, L. J. Chem. Research(s). 1994,506-507. Briffaud, T.; Larpent, C.; Patin, H. J. Chem. Soc.Chem.Commun. 1990, 1193-1194. Kim, S.B.; Lee, K.W.; Kim, Y. J.; Hong, S. I. Bull. Korean Chem. Soc. 1994, 15, 424-427. Lee, K.-W.; Kim, S. B.; Jun, K.W.; Shim, E. K. New. J. Chem., 1993, 17, 409-411 and references there cited..
11. 4 For other significant contributions to Gif chemistry see: Cofré, P.; Richert, S. A.; Sobkowiak, A.; Sawyer, D. T. Inorg. Chem. 1990, 29, 2645-2651.; Tung, H.C.; Kang, C.; Sawyer, D. T. J. Am. Chem. Soc. 1992, 114, 3445-3455 and references cited therein. Schuchardt, U.; Krähembühl, E. Z.,; Carvalho, W. A.; New J. Chem. 1991, 15, 955-958. Schuchardt, U.; Carvalho, W. A.; Spinacé, E. V. Synlett 1993, 713-718 and references there cited. Powell, G.; Richens, D. T.; Khan, L. J. Chem. Research(s). 1994,506-507. Briffaud, T.; Larpent, C.; Patin, H. J. Chem. Soc.Chem.Commun. 1990, 1193-1194. Kim, S.B.; Lee, K.W.; Kim, Y. J.; Hong, S. I. Bull. Korean Chem. Soc. 1994, 15, 424-427. Lee, K.-W.; Kim, S. B.; Jun, K.W.; Shim, E. K. New. J. Chem., 1993, 17, 409-411 and references there cited..
12. 4 For other significant contributions to Gif chemistry see: Cofré, P.; Richert, S. A.; Sobkowiak, A.; Sawyer, D. T. Inorg. Chem. 1990, 29, 2645-2651.; Tung, H.C.; Kang, C.; Sawyer, D. T. J. Am. Chem. Soc. 1992, 114, 3445-3455 and references cited therein. Schuchardt, U.; Krähembühl, E. Z.,; Carvalho, W. A.; New J. Chem. 1991, 15, 955-958. Schuchardt, U.; Carvalho, W. A.; Spinacé, E. V. Synlett 1993, 713-718 and references there cited. Powell, G.; Richens, D. T.; Khan, L. J. Chem. Research(s). 1994,506-507. Briffaud, T.; Larpent, C.; Patin, H. J. Chem. Soc.Chem.Commun. 1990, 1193-1194. Kim, S.B.; Lee, K.W.; Kim, Y. J.; Hong, S. I. Bull. Korean Chem. Soc. 1994, 15, 424-427. Lee, K.-W.; Kim, S. B.; Jun, K.W.; Shim, E. K. New. J. Chem., 1993, 17, 409-411 and references there cited..
13. 5 (a) Bardin, C.; Barton, D. H. R.; Hu, B.; Rojas Wahl, R. U.; Taylor, D. K. Tetrahedron Lett. 1994, 35, 5805-5808.
14. (b) Barton, D. H. R.; Chabot, B.M; Delanghe, N. C.; Hu, B.; Le Gloahec, V. N.and Rojas Wahl, R. U.Ibib. 1995, 36, 7007-7010.
15. 6 (a) Barton, D. H. R.; Bévière, S. D.; Chavasiri, W.; Csuhai, E; Doller, D.; Liu, W. G.; Reibenspies, J. H. New. J. Chem. 1992, 16, 1019-1029.;
16. (b) Sawyer, D.T.; Kang, C.; Llobet, A.; Redman, C. J. Am. Chem. Soc. 1993, 115, 5817-5818.
17. 7 Cercek, B.; Ebert, M. Trans. Faraday Soc. 1967, 63, 1687-1698.
18. 8 Barton, D. H. R.; Bévière, S. D. Tetrahedron Lett. 1993, 34, 5689-5692.
19. 9 Titrated according to: Clark, L. J. Analytical Chemistry 1962, 34, 348-352.
20. 10 Barton, D. H. R.; Bévière, S. D.; Chavasiri, W.; Csuhai, E.; Doller, D.; Liu, W. G. J. Am. Chem. Soc. 1992, 114, 2147-2156 and references therein.
21. 11 Bowry, V. W.; Lusztyk, J.; Ingold, K. U. J. Am. Chem. Soc., 1991, 113, 5687-5698.; Bowry, V. W.; Lusztyk, J.; Ingold, K. U. ibid. 1989, 111, 1927-1928. Chateauneuf, J.; Lusztyk, J.; Ingold, K. U. ibid. 1988, 110, 2877-2885.
22. 11 Bowry, V. W.; Lusztyk, J.; Ingold, K. U. J. Am. Chem. Soc., 1991, 113, 5687-5698.; Bowry, V. W.; Lusztyk, J.; Ingold, K. U. ibid. 1989, 111, 1927-1928. Chateauneuf, J.; Lusztyk, J.; Ingold, K. U. ibid. 1988, 110, 2877-2885.
23. 11 Bowry, V. W.; Lusztyk, J.; Ingold, K. U. J. Am. Chem. Soc., 1991, 113, 5687-5698.; Bowry, V. W.; Lusztyk, J.; Ingold, K. U. ibid. 1989, 111, 1927-1928. Chateauneuf, J.; Lusztyk, J.; Ingold, K. U. ibid. 1988, 110, 2877-2885.
24. 12 Newcomb, M. Tetrahedron, 1993, 49, 1151-1176.
25. 13 Barton, D.H.R., Jaszberenyi J. Cs., Tang, D., Tetrahedron Lett. 1993, 34, 3381-3384. This lamp is a Brinkmann® Beam® Max Million™ one million candlepower spotlight. This is available inexpensively from the Brinkmann Corp. 4215 McEwen Rd., Dallas, TX 75244.
26. 14 Hunter, D. H.; Barton, D. H. R.; Motherwell, W. J. Tetrahedron Lett. 1984, 20, 603-606.
27. 15 Rozantsev, E. G.; Sholle, V. D. Synthesis 1971, 401-414.; Ganem, B. J. Org. Chem. 1975, 40, 1998-2000.; Semmelhack, M. F.; Schmid, C. R.; Cortes, D. A.; Chou, C. S. J. Am. Chem. Soc. 1984, 106, 3374-3376.; Inokuchi, T.; Nakagawa, K.; Torii, S. Tetrahedron Lett. 1995, 36, 3223-3226.
28. 15 Rozantsev, E. G.; Sholle, V. D. Synthesis 1971, 401-414.; Ganem, B. J. Org. Chem. 1975, 40, 1998-2000.; Semmelhack, M. F.; Schmid, C. R.; Cortes, D. A.; Chou, C. S. J. Am. Chem. Soc. 1984, 106, 3374-3376.; Inokuchi, T.; Nakagawa, K.; Torii, S. Tetrahedron Lett. 1995, 36, 3223-3226.
29. 15 Rozantsev, E. G.; Sholle, V. D. Synthesis 1971, 401-414.; Ganem, B. J. Org. Chem. 1975, 40, 1998-2000.; Semmelhack, M. F.; Schmid, C. R.; Cortes, D. A.; Chou, C. S. J. Am. Chem. Soc. 1984, 106, 3374-3376.; Inokuchi, T.; Nakagawa, K.; Torii, S. Tetrahedron Lett. 1995, 36, 3223-3226.
30. 15 Rozantsev, E. G.; Sholle, V. D. Synthesis 1971, 401-414.; Ganem, B. J. Org. Chem. 1975, 40, 1998-2000.; Semmelhack, M. F.; Schmid, C. R.; Cortes, D. A.; Chou, C. S. J. Am. Chem. Soc. 1984, 106, 3374-3376.; Inokuchi, T.; Nakagawa, K.; Torii, S. Tetrahedron Lett. 1995, 36, 3223-3226.
31. 16 Kaeding, W.W. J. Org. Chem. 1963, 28, 1063-1067. Horswill, E. C.; Ingold, K.U. Can. J. Chem. 1966, 44, 269-277. Armstrong, D. R.; Cameron, C.; Nonhebel, D. C.; Perkins, P. G. J. Chem. Soc.(Perkin Trans. II) 1983, 587-589.
32. 16 Kaeding, W.W. J. Org. Chem. 1963, 28, 1063-1067. Horswill, E. C.; Ingold, K.U. Can. J. Chem. 1966, 44, 269-277. Armstrong, D. R.; Cameron, C.; Nonhebel, D. C.; Perkins, P. G. J. Chem. Soc.(Perkin Trans. II) 1983, 587-589.
33. 16 Kaeding, W.W. J. Org. Chem. 1963, 28, 1063-1067. Horswill, E. C.; Ingold, K.U. Can. J. Chem. 1966, 44, 269-277. Armstrong, D. R.; Cameron, C.; Nonhebel, D. C.; Perkins, P. G. J. Chem. Soc.(Perkin Trans. II) 1983, 587-589.
34. 12 at 0°C to RT.
35. 18 Farcasiu, D. Synthesis 1972, 615-616.
36. 19 Barton, D. H. R. Aldrichimica Acta. 1990, 23, 3-11.
37. 20 Malysheva, R. D.; Ershov, V. V. and Volod'kin, A. A. Izv. Akad. Nauk. SSSR, Ser. Khim. 1983, 610-613.