Type B semiconductor photocatalysis: The synthesis of homoallyl amines by cadmium sulfide-catalyzed linear photoaddition of olefins and enol/allyl ethers to N-phenylbenzophenone imine

Chemistry - A European Journal

Volumn 3, Issue 10, 1997, Pages 1638-1645

  Keck, Helmut ^b   Schindler, Wolfram ^b   Knoch, Falk ^b   Kisch, Horst ^a  

^a UNIVERSITY OF ERLANGEN NUREMBERG   (Germany)

^b NONE

Author keywords

Cadmium sulfide; Catalysis; Photochemistry; Semiconductors; Unsaturated amines

Indexed keywords

EID: 0030750805     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.19970031013     Document Type: Article

References (58)

1. a) N. Zeug, J. Bücheler, H. Kisch, J. Am. Chem. Soc. 1985, 107, 1459;
2. b) R. Künneth, G. Twardzik, G. Emig, H. Kisch, J. Photochem. Photobiol. A.: Chem. 1993, 76, 209;
3. c) S. Yanagida, H. Kawakami, Y. Midori, H. Kizumoto, C. Pac, Y. Wada, Bull. Chem. Soc. Jpn. 1995, 68, 1811.
4. a) R. Künneth, C. Feldmer, H. Kisch, Angew. Chem. 1992, 104, 1102; Angew. Chem. Int. Ed. Engl. 1992, 31, 1039;
5. a) R. Künneth, C. Feldmer, H. Kisch, Angew. Chem. 1992, 104, 1102; Angew. Chem. Int. Ed. Engl. 1992, 31, 1039;
6. b) R. Künneth, C. Feldmer, F. Knoch, H. Kisch, Chem. Eur. J. 1995, 1, 441.
7. W. Schindler, H. Kisch, Chem. Ber. 1996, 129, 925.
8. C. Amatore, A. R. Brown, J. Am. Chem. Soc. 1996, 118, 1482.
9. J. March, Advanced Organic Chemistry, 4th ed., Wiley, New York, 1992, p. 21.
10. M. J. Begley, G. B. Gill, B. Wallace, J. Chem. Soc. Perkin Trans. 1 1978, 93.
11. R. J. Abraham, M. A. Cooper, J. R. Salmon, D. Whittaker, Org. Magn. Reson. 1972, 4, 489.
12. a) W. Offermann, Org. Magn. Reson. 1982, 20, 203;
13. b) W. Offermann, A. Mannschreck, ibid. 1984, 22, 355.
14. C. W. Haigh, R. B. Mallion, Org. Magn. Reson. 1972, 4, 203.
15. a) A. Mills, G. Williams, J. Chem. Soc. Faraday Trans. 1 1987, 83, 2647;
16. b) J. R. Harbour, R. Wolkow, M. L. Hair, J. Phys. Chem. 1981, 85, 4026;
17. c) M. V. Rao, K. Rajeshwar, V. R. Pal Vernekey, J. Du Bow, J. Phys. Chem. 1980, 84, 1987,
18. d) J. Cunningham, B. K. Hodnett, J. Chem Soc. Faraday Trans. 1 1987, 77, 2777.
19. a) M. Fischer, Tetrahedron 1966, 43, 5273;
20. b) M. Fischer, Chem. Ber. 1967, 100, 3599.
21. H. Lund, J. Simonet, Bull. Soc. Chim. Fr. 1973, 5, 1843.
22. a) J. G. Smith, C. D. Veach, Can. J. Chem. 1966, 44, 2245;
23. b) J. G. Smith, ibid. 1968, 46, 2271;
24. c) J. G. Smith, R. A. Turle, J. Org. Chem. 1972, 37, 126;
25. d) J. G. Smith, I. Ho, ibid. 1972, 37, 653;
26. e) J. G. Smith, G. E. F. Simpson, ibid. 1976, 41, 2878;
27. f) J. G. Smith, D. J. Mitchell, J. Am. Chem. Soc. 1977, 99, 5045;
28. g) J. G. Smith, D. C. Irwin, ibid. 1980, 102, 2757.
29. K. Harada, The Chemistry of the Carbon-Nitrogen Double Bond (Ed.: S. Patai), Interscience, New York, 1970.
30. K. Takaki, Y. Tsubaki, S. Tanaka, F. Beppu, Y. Fujiwara, Chem. Lett. 1990, 203.
31. H. Thies, H. Schönberger, K. H. Bauer, Arch. Pharmaz. 1960, 293, 67.
32. a) H. Lund, Acta Chem. Scand. 1959, 13, 249;
33. b) C. P Andrieux, J. M. Saveánt, J. Electroanal. Chem. 1970, 26, 223.
34. a) D. Meissner, R. Memming, B. Kastening, J. Phys. Chem. 1988, 92, 3476;
35. b) D. Meissner, I. Lauermann, R. Memming, B. Kastening, ibid. 1988, 92, 3484;
36. c) M. F. Finlayson, B. L. Wheeler, N. Kakuta, K.-H. Park, A. J. Bard, A. Campion, M. A. Fox, S. E. Webber, J. M. White, ibid. 1985, 89, 5676;
37. d) D. S. Ginley, M. A. Butler, J. Electrochem. Soc. 1978, 125, 1968;
38. e) A. M. Roy, G. C. De, N. Sasmal, S. S. Bhattacharyya, Int. J. Hydrogen Energy 1995, 30 No. 8, 627.
39. R. Knorr, K. Ferchland, Liebigs Ann. 1995, 419.
40. a) W. Schindler, Ph.D. Thesis, Üniversität Erlangen-Nürnberg, 1996;
41. .+ and 2.5-DHF, respectively;
42. +/H) = -2.1 V and a C-H bond dissociation energy of 3.7 eV as obtained from ref. [20e]. The same argument was used to explain the photooxidation of alcohols by ZnS [20d];
43. d) A. Henglein, M. Gutierrez, Ch.-H. Fischer. Ber. Bunsenges. Phys. Chem. 1984, 88, 170.
44. e) R. T. Sanderson, Chemical Bond and Bond Energy. Academic Press, New York, 1976.
45. 4, was isolated in 65% yield [20a].
46. a) M. Anpo, A. Matsumoto, S. Kodama, J. Chem. Soc., Chem. Commun. 1987, 1038;
47. b) Y. Nakaoka, Y. Nosaka, J. Phys. Chem. 1995, 99, 9893;
48. c) P. V. Kamat, N. M. Dimitrijevic, R. W. Fessenden, J. Phys. Chem. 1987, 91, 396.
49. d) L. Lunazzi, G. Placucci, L. Grossi. Tetrahedron 1983, 39, 159.
50. e) See, for example, A. Nozik, R. Memming, J. Phys. Chem. 1996, 1306.
51. .+: A. Albini, M. Mella, M. Freccero. Tetrahedron 1994, 50, 575.
52. G. Reddelien, Ber. 1913, 46, 2718.
53. ox = 0.89 × IP - 6.04 + 0.49; L. Miller, G. D. Nordblom, E. A. Mayeda, J. Org. Chem. 1972, 37, 916.
54. a) D. A. Demeo, M. A. El-Sayed, J. Chem. Phys. 1970, 52, 2622;
55. b) M. Bloch, F. Brogli, E. Heilbronner, T. B. Jones, H. Prinzbach, O. Schweikert, Helv. Chim. Acta 1978, 61, 1388.
56. K. Kimura, S. Katsumata, T. Achiba, S. Iwata, Handbook of Photoelectron Spectra of Fundamental Organic Molecules Japan Scientific: Tokyo, Halsted Press, New York, 1981; P. Bischof, E. Heilbronner, Helv. Chim. Acta 1970, 53, 1677.
57. K. Kimura, S. Katsumata, T. Achiba, S. Iwata, Handbook of Photoelectron Spectra of Fundamental Organic Molecules Japan Scientific: Tokyo, Halsted Press, New York, 1981; P. Bischof, E. Heilbronner, Helv. Chim. Acta 1970, 53, 1677.
58. J. Amrein, J. Gloor, K. Schaffner, Chimia 1974, 29, 185.