Photodynamics of the Paterno-Büchi cycloaddition of stilbene to quinone. Unusual modulation of electron-transfer kinetics by solvent and added salt

Journal of the Chemical Society. Perkin Transactions 2

Volumn , Issue 4, 1999, Pages 781-788

  Hubig, Stephan M ^a   Sun, Duoli ^a   Kochi, Jay K ^a  

^a University of Houston   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001266023     PISSN: 03009580     EISSN: None     Source Type: Journal    
DOI: 10.1039/a809595g     Document Type: Article

References (64)

1. J.-H. Xu, L.-C. Wang, J.-W. Xu, B.-Z. Yan and H.-C. Yuan, J. Chem. Soc., Perkin Trans. 1, 1994, 571.
2. D. Sun, S. M. Hubig and J. K. Kochi, J. Org. Chem., in the press.
3. E. Paterno and G. Chieffi, Gazz. Chim. Ital., 1909, 39, 341; G. Büchi, C. G. Inman and E. S. Lipinsky, J. Am. Chem. Soc., 1954, 76, 4327.
4. E. Paterno and G. Chieffi, Gazz. Chim. Ital., 1909, 39, 341; G. Büchi, C. G. Inman and E. S. Lipinsky, J. Am. Chem. Soc., 1954, 76, 4327.
5. 8-12
6. R. A. Caldwell, D. C. Hrncir, T. Muñoz, Jr. and D. J. Unett, J. Am. Chem. Soc., 1996, 118, 8741; R. A. Caldwell, G. W. Sovocool and R. P. Gajewski, J. Am. Chem. Soc., 1973, 95, 2549; N. E. Schore and N. J. Turro, J. Am. Chem. Soc., 1975, 97, 2482.
7. R. A. Caldwell, D. C. Hrncir, T. Muñoz, Jr. and D. J. Unett, J. Am. Chem. Soc., 1996, 118, 8741; R. A. Caldwell, G. W. Sovocool and R. P. Gajewski, J. Am. Chem. Soc., 1973, 95, 2549; N. E. Schore and N. J. Turro, J. Am. Chem. Soc., 1975, 97, 2482.
8. R. A. Caldwell, D. C. Hrncir, T. Muñoz, Jr. and D. J. Unett, J. Am. Chem. Soc., 1996, 118, 8741; R. A. Caldwell, G. W. Sovocool and R. P. Gajewski, J. Am. Chem. Soc., 1973, 95, 2549; N. E. Schore and N. J. Turro, J. Am. Chem. Soc., 1975, 97, 2482.
9. S. Hu and D. C. Neckers, J. Org. Chem., 1997, 62, 6820.
10. J. Gersdorf, J. Mattay and H. Görner, J. Am. Chem. Soc., 1987, 109, 1203.
11. S. C. Freilich and K. S. Peters, J. Am. Chem. Soc., 1985, 107, 3819; J. Am. Chem. Soc., 1981, 103, 6255.
12. S. C. Freilich and K. S. Peters, J. Am. Chem. Soc., 1985, 107, 3819; J. Am. Chem. Soc., 1981, 103, 6255.
13. A. G. Griesbeck, H. Mauder and S. Stadtmüller, Acc. Chem. Res., 1994, 27, 70.
14. G. Eckert and M. Goez, J. Am. Chem. Soc., 1994, 116, 11999.
15. D. I. Schuster, G. Lem and N. A. Kaprinidis, Chem. Rev., 1993, 93, 3.
16. S. Hu and D. C. Neckers, J. Org. Chem., 1997, 62, 564.
17. For reviews, see: G. Jones II, in Organic Photochemistry, ed. A. Padwa, Dekker, New York, 1981, vol. 5, p. 1; A. G. Griesbeck, in CRC Handbook of Organic Photochemistry and Photobiology, ed. W. M. Horspool and P.-S. Song, CRC Press, Boca Raton, FL, 1995, p. 522.
18. For reviews, see: G. Jones II, in Organic Photochemistry, ed. A. Padwa, Dekker, New York, 1981, vol. 5, p. 1; A. G. Griesbeck, in CRC Handbook of Organic Photochemistry and Photobiology, ed. W. M. Horspool and P.-S. Song, CRC Press, Boca Raton, FL, 1995, p. 522.
19. R. Rathore, S. M. Hubig and J. K. Kochi, J. Am. Chem. Soc., 1997, 119, 11468, and references therein.
20. E. Bosch, S. M. Hubig and J. K., Kochi, J. Am. Chem. Soc., 1998, 120, 386.
21. R. Gschwind and E. Haselbach, Helv. Chim. Acta, 1979, 62, 941.
22. S. M. Hubig, T. M. Bockman and J. K. Kochi, J. Am. Chem. Soc., 1997, 119, 2926.
23. red = 2.15 V vs. SCE. See ref. 14.
24. ox ≅ 1.56 V vs. SCE. See ref 23.
25. 8-12
26. (a) K. S. Peters, Adv. Electron Transfer Chem., 1994, 4, 27;
27. (b) M. A. Fox, Adv. Photochem., 1986, 13, 237;
28. H. Knibbe, D. Rehm and A. Weller, Ber. Bunsenges. Phys. Chem., 1968, 72, 257.
29. max = 320 nm. See J. J. André and G. Weill, Mol. Phys., 1968, 15, 97.
30. max = 480 and 760 nm. See: F. D. Lewis, A. M. Bedell, R. E. Dykstra, J. E. Elbert, I. R. Gould and S. Farid, J. Am. Chem. Soc., 1990, 112, 8055; T. Shida, Electronic Absorption Spectra of Radical Ions, Elsevier, New York, 1988, p. 112.
31. max = 480 and 760 nm. See: F. D. Lewis, A. M. Bedell, R. E. Dykstra, J. E. Elbert, I. R. Gould and S. Farid, J. Am. Chem. Soc., 1990, 112, 8055; T. Shida, Electronic Absorption Spectra of Radical Ions, Elsevier, New York, 1988, p. 112.
32. C. G. Hatchard and C. A. Parker, Proc. R. Soc London, Ser. A, 1956, 235, 518. See also: J. G. Calvert and J. N. Pitts, Jr., Photochemistry, Wiley, New York, 1996, p. 786.
33. C. G. Hatchard and C. A. Parker, Proc. R. Soc London, Ser. A, 1956, 235, 518. See also: J. G. Calvert and J. N. Pitts, Jr., Photochemistry, Wiley, New York, 1996, p. 786.
34. C. Reichardt, Solvent Effects in Organic Chemistry, Verlag Chemie, New York, 1979.
35. rd edn., CRC Press, Boca Raton, FL, 1975, p. E73.
36. D. Bryce-Smith, B. F. Connett and A. Gilbert, J. Chem. Soc (B), 1968, 816; M. A. Slifkin, Spectrochim. Acta, Part A, 1969, 25, 1037.
37. D. Bryce-Smith, B. F. Connett and A. Gilbert, J. Chem. Soc (B), 1968, 816; M. A. Slifkin, Spectrochim. Acta, Part A, 1969, 25, 1037.
38. H. Benesi and J. H. Hildebrand, J. Am. Chem. Soc., 1949, 71, 2703; W. B. Person, J. Am. Chem. Soc., 1965, 87, 167.
39. H. Benesi and J. H. Hildebrand, J. Am. Chem. Soc., 1949, 71, 2703; W. B. Person, J. Am. Chem. Soc., 1965, 87, 167.
40. J. N. Murrell, J. Am. Chem. Soc., 1954, 81, 5037.
41. rd edn., Wiley, New York, 1981, p. 239.
42. -1. See ref. 30.
43. T. Asahi and N. Mataga, J. Phys. Chem., 1989, 93, 6575; 1991, 95, 1956.
44. T. Asahi and N. Mataga, J. Phys. Chem., 1989, 93, 6575; 1991, 95, 1956.
45. E. F. Hilinki, J. M. Masnovi, J. K. Kochi and P. M. Rentzepis, J. Am. Chem. Soc., 1984, 106, 8071.
46. S. Ojima, H. Miyasaka and N. Mataga, J. Phys. Chem., 1990, 94, 4147.
47. H. Kobashi, M.-A. Funabashi, T. Kondo, T. Morita, T. Okada and N. Mataga, Bull. Chem. Soc. Jpn., 1984, 57, 3557; H. Kobashi, T. Okada and N. Mataga, Bull. Chem. Soc. Jpn., 1986, 59, 1975; G. Jones II, W. A. Haney and X. T. Phan, J. Am. Chem. Soc., 1988, 110, 1922.
48. H. Kobashi, M.-A. Funabashi, T. Kondo, T. Morita, T. Okada and N. Mataga, Bull. Chem. Soc. Jpn., 1984, 57, 3557; H. Kobashi, T. Okada and N. Mataga, Bull. Chem. Soc. Jpn., 1986, 59, 1975; G. Jones II, W. A. Haney and X. T. Phan, J. Am. Chem. Soc., 1988, 110, 1922.
49. H. Kobashi, M.-A. Funabashi, T. Kondo, T. Morita, T. Okada and N. Mataga, Bull. Chem. Soc. Jpn., 1984, 57, 3557; H. Kobashi, T. Okada and N. Mataga, Bull. Chem. Soc. Jpn., 1986, 59, 1975; G. Jones II, W. A. Haney and X. T. Phan, J. Am. Chem. Soc., 1988, 110, 1922.
50. -1. (b) It is not clear at this stage why the hydrogen abstraction is suppressed in the presence of high amounts of inert salt.
51. S. Ojima, H. Miyasaka and N. Mataga, J. Phys. Chem., 1990, 94, 7534.
52. C) of chloranil anion radical and stilbene cation radical to the 1,4-biradical intermediate represents the first (rate-determining) step toward oxetane formation by analogy with the biradical intermediates observed in the Paterno-Büchi coupling of benzoquinone and styrene. See: K. Maruyama, T. Otsuki and S. Tai, J. Org. Chem., 1985, 50, 52; K. Maruyama and H. Imahori, J. Org. Chem., 1989, 54, 2692. Note that in our study no further transient intermediates have been detected upon the decay of the ion-radical pairs.
53. C) of chloranil anion radical and stilbene cation radical to the 1,4-biradical intermediate represents the first (rate-determining) step toward oxetane formation by analogy with the biradical intermediates observed in the Paterno-Büchi coupling of benzoquinone and styrene. See: K. Maruyama, T. Otsuki and S. Tai, J. Org. Chem., 1985, 50, 52; K. Maruyama and H. Imahori, J. Org. Chem., 1989, 54, 2692. Note that in our study no further transient intermediates have been detected upon the decay of the ion-radical pairs.
54. 2
55. 14,16
56. S. M. Hubig, W. Jung and J. K. Kochi, J. Org. Chem., 1994, 59, 6233; T. Yabe and J. K. Kochi, J. Am. Chem. Soc., 1992, 114, 4491.
57. S. M. Hubig, W. Jung and J. K. Kochi, J. Org. Chem., 1994, 59, 6233; T. Yabe and J. K. Kochi, J. Am. Chem. Soc., 1992, 114, 4491.
58. C.
59. F. D. Lewis, J. R. Petisce, J. D. Oxman and M. J. Nepras, J. Am. Chem. Soc., 1985, 107, 203; Y. Kuriyama, H. Sakuragi, K. Tokumaru, Y. Yoshida and S. Tagawa, Bull. Chem. Soc. Jpn., 1993, 66, 1852; A. Corma, V. Fornés, H. Garcia. M. A. Miranda, J. Primo and M. Sabater, J. Am. Chem. Soc., 1994, 116, 2276.
60. F. D. Lewis, J. R. Petisce, J. D. Oxman and M. J. Nepras, J. Am. Chem. Soc., 1985, 107, 203; Y. Kuriyama, H. Sakuragi, K. Tokumaru, Y. Yoshida and S. Tagawa, Bull. Chem. Soc. Jpn., 1993, 66, 1852; A. Corma, V. Fornés, H. Garcia. M. A. Miranda, J. Primo and M. Sabater, J. Am. Chem. Soc., 1994, 116, 2276.
61. F. D. Lewis, J. R. Petisce, J. D. Oxman and M. J. Nepras, J. Am. Chem. Soc., 1985, 107, 203; Y. Kuriyama, H. Sakuragi, K. Tokumaru, Y. Yoshida and S. Tagawa, Bull. Chem. Soc. Jpn., 1993, 66, 1852; A. Corma, V. Fornés, H. Garcia. M. A. Miranda, J. Primo and M. Sabater, J. Am. Chem. Soc., 1994, 116, 2276.
62. nd edn., Pergamon, New York, 1980.
63. T. M. Bockman and J. K. Kochi, J. Chem. Soc., Perkin Trans. 2, 1996, 1633.
64. S. M. Hubig, T. M. Bockman and J. K. Kochi, J. Am. Chem. Soc., 1996, 118, 3842.