Photochemical and chemical electron transfer reactions of bicyclo[2.1.0]pentanes (housanes) in solution and in zeolite cavities

Journal of the American Chemical Society

Volumn 118, Issue 10, 1996, Pages 2380-2386

  Adam, Waldemar ^a   Corma, Avelino ^a   Miranda, Miguel A ^a   Sabater Picot, Maria José ^a   Sahin, Coskun ^a  

^a UNIVERSITY OF WÜRZBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

BICYCLO COMPOUND; BICYCLO[2.1.0]PENTANE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ELECTRON TRANSPORT; PHOTOCHEMISTRY;

EID: 0029864378     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja950397k     Document Type: Article

References (72)

1. (a) Kavamos, G. J.; Turro, N. J. Chem. Rev. 1986, 86,401 -449.
2. (b) Sakurasi, H.: Nakagaki. R.; Oguchi. T.; Arai. T.; Tokumaru, K.; Nagakura, S. Chem. Phys. Lett. 1987.135, 325-329.
3. (c) Oguchi, T.; Arai, T.; Sakuragi, H.; Tokumaru, K. Bull. Chem. Soc. Jpn. 1987, 60, 2395-2399.
4. (d) Julliard, M.; Chanon, M. Chem. Rev. 1983. 83, 425-506.
5. (e) Fox, M. A., Chanon, M.. Eds. Photoinduced Electron Transfer. Eisevier: Amsterdam, 1988.
6. (a) Martay, J. Angew. Chem., Int. Ed. Engl. 1987, 26, 825-845.
7. (b) Mattay, J. Synthesis 1989, 223-252.
8. (c) Fand. S.; Martes, S. L. In Organic Photochemistry: Padwa. A.. Ed.; Marcel Dekker: New York, 1983; Vol. 6. pp 233-326.
9. (d) Fox, M. A. In Advanced Photochemistry: Volman, D. H., Hammond, G. S., Gollnick, K., Eds.; J. Wiley & Sons: New York, 1986; Vol. 13. pp 237-327.
10. (e) Kavarnos, G. J. Top. Curr. Chem. 1990, 156, 21-58.
11. (a) Adam, W.; Sahin, C; Sendelbach, J.; Walter, H.; Chen, G.-F.; Williams, F. J. Am. Chem. Soc. 1994, 116, 2576-2584.
12. (b) Adam, W.; Sendelbach, J. J. Org. Chem. 1993, 58, 5316-5322.
13. (c) Adam, W.; Sendelbach, J. J. Org. Chem. 1993, 58, 5310-5315.
14. (d) Adam, W.; Denninger, U.; Finzel, R.; Kita, F.; Platsch, H.; Walter, H.; Zang, G. J Am. Chem. Soc. 1992, 114. 5027-5035.
15. (e) Adam, W.; Walter, H.; Chen, G.-F.; Williams, F. J. Am. Chem. Soc. 1992, 114, 3007-3014.
16. (f) Adam, W.; Dörr, M. J. Am. Chem. Soc. 1987, 109, 1570-1572.
17. Gould, I. R.; Young, R. H.; Moody, R. E.; Farid, S. J. Phys. Chem. 1991, 95, 2068-2080.
18. (a) Gould, L R.; Ege, D.; Mooser, J. E.; Farid, S. J. Am. Chem. Soc. 1990, 112, 4290-4301.
19. (b) Julliard, M. In Photoinduced Electron Transfer, Fox, M. A., Chanon, M., Eds.; Elsevier: Amsterdam, 1988; Part B, pp 216-313.
20. (c) Schaap, A. P.; Siddiqui, S.; Prasad, G.; Palomino, E.; Lopez. L. J. Phorochem. 1984, 25, 167-181.
21. (d) Arnold, D. R.; Snow, M. S. Can. J. Chem. 1988. 66, 3012-3026.
22. (e) Majiama, T.; Pac, C; Nakasone, A.; Sakurai, H. J. Am. Chem. Soc. 1981, 103, 4499-4508.
23. Adam, W.; Sahin, C. Tetrahedron Lett. 1994. 35, 9027-9030.
24. Schmidt, W.; Steckhan, E. Chem. Ber. 1980, 113, 577-585.
25. (a) Corma, A.; Fernes, V.; Garcia, H.; Miranda. M. A.: Primo, J.; Sabater. M. J. J. Am. Chem. Soc. 1994, 116, 2276-2280.
26. (b) Corma, A.; Fomés, V.; Garcia, H.; Miranda, M. A.; Sabater, M. J. J. Am. Chem. Soc. 1994, 116, 9767-9768.
27. (c) Corma. A.; Garcia, H.; Iborra, S.; Marti, V.; Miranda, M. A.: Primo, J. J. Am. Chem. Soc. 1993, 175, 2177-2180.
28. (d) Alvaro. M.; Corma, A.; Garcia. H.; Miranda. M. A.; Primo, J. J. Chem. Soc., Chem. Commun. 1993, 1041-1042.
29. (e) Corma, A.; Fornés, V.; Rey, F. Appl. Catal. 1990, 59, 267-274.
30. Miranda, M. A.; Garcia, H. Chem. Rev. 1994, 94. 1063-1089.
31. (a) Ramamurthy, V., Ed. Photochemistry in Organized and Constrained Media; Verlag Chemie: New York, 1991.
32. (b) Ramamurthy, V.; Caspar, J. V.; Corbin, D. R. J. Am. Chem. Soc. 1991. 113. 594-600.
33. (c) Gessner. F.: Scaiano, J. C. J. Photockem. Photobiol, A 1992. 67, 91-100.
34. (d) Sankararaman, S.; Yoon, K. B.; Yobe, T.L Kochi, J. K. J. Am. Chem. Soc. 1991. 113, 1419-1421.
35. (a) Gassman, P. G.; Mansfield. K. T. Org. Synth. 1969, 49, 1-6.
36. (b) Criegee. R.: Rimmelin. A. Chem. Ber. 1957, 90, 414-417.
37. Wilson. R. M.; Rekers. J. W.; Packard, A. B.; Elder, R. C. J. Am. Chem. Soc. 1980, 102, 1633-1641.
38. Adam, W.; Grabowski, S.; Platsch, H.; Hannemann, K.; Wirz, J.; Wilson. R. M. J. Am. Chem. Soc. 1989, 111, 751-753.
39. (a) Beck. K.; Hiinig. S. Chem. Ber. 1987, 120, 477-483.
40. (b) Beck, K.; Höhn, A.; Hünig. S.; Prokschy, F. Chem. Ber. 1984. 117, 517-533.
41. Adam. W.: Sahin, C.: Schneider, M. J. Am. Chem. Soc. 1995, 117, 1695-1702.
42. Usually the cancerogenic hexamethylphosphoric triamide is used in activating vinylcuprates, cf.: Alexakis, A.; NormanL J. J. Organomet. Chem. 1975, 96, 471-485. Alexakis, A.; Cahiez, G.; Normant, J. F. Synthesis 1979, 826-830.
43. Usually the cancerogenic hexamethylphosphoric triamide is used in activating vinylcuprates, cf.: Alexakis, A.; NormanL J. J. Organomet. Chem. 1975, 96, 471-485. Alexakis, A.; Cahiez, G.; Normant, J. F. Synthesis 1979, 826-830.
44. For related systems see ref. 3e and also the following Paquerte, L. A.: Leichter. L. M. J. Am. Chem. Soc. 1971, 93, 5128-5136.
45. (a) Adam, W.; DeLucchi, O. Angew. Chem. 1980, 92, 815-832; Angew. Chem., Im. Ed. Engl. 1980, 762.
46. (a) Adam, W.; DeLucchi, O. Angew. Chem. 1980, 92, 815-832; Angew. Chem., Im. Ed. Engl. 1980, 762.
47. (b) Engel, P. S. Chem. Rev. 1980, 80. 99-150.
48. Adam, W.; Oppenländer, T.; Zang, G. J. Org. Chem. 1985, 50, 3303-3312.
49. Wiberg. K. B.; Kass. S. R.; Bishop, K. C., III J. Am. Chem. Soc. 1985, 107, 996-1002.
50. McKinney, M. A.; Chou, S. K. Tetrahedron Lett. 1974, 1145-1148.
51. (a) Descoins. C.; Julia, M.; Sang, H. V. Bull. Soc. Chim. Fr. 1971, 4087-4093.
52. (b) Ohbe, Y.; Matsuda, T. Bull. Chem. Soc. Jpn. 1975, 48, 2389-2390.
53. (a) von Braun, J.; Kühn, M. Ber. Dtsch. Chem. Ges. 1927, 60. 2551-2557.
54. (b) von Braun. J.; Kamp. E.; Kopp, J. Ibid. 1937. 70, 1750-1760.
55. Rei. M. H. J. Org. Chem. 1978, 43. 2173-2178.
56. Sisido. K.; Kurozumi, S.; Utimoto, K.; Isida. T. J. Org. Chem. 1966. 31, 2795-2802.
57. (a) Vaveck, D.; Jaques. J. Bull. Soc. Chim. Fr. 1969, 10. 3505-3515.
58. (b) Richer. J. C.: Belanger, P. Can. J. Chem. 1966, 44. 2057-2066.
59. Gajewski, J. J.; Squicciarini. M. P. J. Am. Chem. Soc. 1989. 11, 6717-6728.
60. (a) Adam. W.; Reinhard. G.; Platsch, H.; Wirz, J. J. Am. Chem. Soc. 1990. 112, 4570-4571.
61. (b) Paquette. L. A.; Leichter, L. M. J. Org. Chem. 1974. 39, 461-467.
62. (a) Gassman, P. G.: Yamaguchi, R. Tetrahedron 1982, 38, 1113-1122.
63. (b) Gassman, P. G.; Yamasuchi. R.; Koser, G. F. J. Org. Chem. 1978, 43. 4392-4393.
64. (a) The (irreversible) oxidation potentials for 2a and 2i are 1.91 and 1.42 V and the (reversible) ones for TDA and TBA are 1.50 and 1.06 V. The cyclovoltammetric measurements were performed in Prof. M. Schmittel's research group at the University of Würzburg, and we are grateful to H. Trenkle for technical assistance,
65. (b) The (irreversible) oxidation potentials for 3a and 3i are 2.03 and 1.58 V.
66. (a) Wayner, D. D. M.; McPhee, D- J.; Griller, D. J. Am. Chem. Soc. 1988, 110, 132-137.
67. (b) Sim, B. A.; Milne, P. H.; Griller, D.; Wayner, D. D. M. J. Am. Chem. Soc. 1990, 112, 6635-6638.
68. (c) The experimental value seems not to be reported and a reviewer suggested the reasonable value of 0.47 V.
69. •+).
70. The AMI method was used, cf.: Dewar, M. J. S.: Zoebisch, E. G.; Healy, E. F.;Stewart, J. J. P. J. Am. Chem. Soc. 1985. 107, 3902-3909 (by-employing the VAMP program on a Silicon Graphics Iris Indigo work-station: Rauhut, G.; Alex, A.; Chandrasekiar, J.; Steinke, T.; Clark, T. VAMP 5.0; Universität Erlangen: Erlangen, FRG, 1993).
71. The AMI method was used, cf.: Dewar, M. J. S.: Zoebisch, E. G.; Healy, E. F.;Stewart, J. J. P. J. Am. Chem. Soc. 1985. 107, 3902-3909 (by-employing the VAMP program on a Silicon Graphics Iris Indigo work-station: Rauhut, G.; Alex, A.; Chandrasekiar, J.; Steinke, T.; Clark, T. VAMP 5.0; Universität Erlangen: Erlangen, FRG, 1993).
72. f values (AMI calculations, see footnote 32) are 172 kcal/ mol for the tetraalkyl- and 184 kcal/mol for the trialky!-substituted olefm 1,2-radical cations.