Intramolecular [σs2 + πs2] photocycloaddition reaction of parallel three-membered rings with azo groups

Liebigs Annales

Volumn , Issue 4, 1996, Pages 575-583

  Hünig, Siegfried ^a   Schmitt, Michael ^a  

^a UNIVERSITY OF WÜRZBURG   (Germany)

Author keywords

Azo bridges; Three membered rings; Transannular reactions; 3 + 2 Photocycloaddition; and excitation

Indexed keywords

EID: 33748913015     PISSN: 09473440     EISSN: None     Source Type: Journal    
DOI: 10.1002/jlac.199619960418     Document Type: Article

References (69)

1. Part XVIII: S. Hünig, M. Schmitt, Liebigs Ann. 1996, 559-573; preceding paper.
2. M. Schmitt, Ph. D. Thesis, University of Würzburg, 1987.
3. K. Beck, S. Hünig, G. Kleefeld, H.-D. Martin, K. Peters, F. Prokschy, H. G. von Schnering, Chem. Ber. 1986, 543-553.
4. B. Albert, W. Berning, Ch. Burschka, S. Hünig, F. Prokschy, Chem. Ber. 1984, 117, 1465-1475.
5. H.-D. Martin, B. Mayer, K. Peters, S. Hünig, F. Prokschy, M. Schmitt, H. G. von Schnering, Chem. Ber. 1987, 120, 195-201.
6. K. Beck, S. Hünig, Chem. Ber. 1987, 120, 477-483.
7. S. Hünig, P. Kraft, Heterocycles 1995, 40, 639-652.
8. S. Hünig, P. Kraft, F.-G. Klärner, U. Artschwager-Perl, K. Peters, H.-G. von Schnering, Liebigs Ann. 1995, 351-156.
9. A. D. Walsh, Trans Faraday Soc. 1949, 45, 179-190.
10. T. M. Sugden, Nature, 1947, 160, 367-368.
11. W. W. Schoeller, Tetrahedron, 1973, 29, 929-931.
12. Cf.: M. Kiessinger, Elektronenstruktur Organischer Moleküle, VCH, Weinheim, 1982.
13. R. B. Woodward, R. Hoffmann, Angew. Chem. 1969, 81, 797-870;
14. Angew. Chem. Int. Ed. Engl. 1969, 8, 781-854.
15. Preliminary publication: S. Hünig, M. Schmitt, Tetrahedron Lett. 1987, 28, 4521-4524.
16. H. G. O. Becker (Ed.), Einführung in die Photochemie, 2nd ed., Thieme Verlag, Stuttgart, 1983.
17. U. Brand, Ph. D. Thesis, University of Würzburg, 1990.
18. W. R. Roth, M. Martin, Tetrahedron Lett. 1967, 8, 4695-4698.
19. M. H. Chang, R. Jain, D. A. Dougherty, J. Am. Chem. Soc. 1984, 106, 4211-4217 and literature cited there.
20. R. Huisgen, W. Scheer, H. Mäder, Angew. Chem. 1969, 81, 619-621;
21. Angew. Chem. Int. Ed. Engl. 1969, 8, 602-604.
22. E. Brunn, R. Huisgen, Tetrahedron Lett. 1971, 12, 473-476.
23. H. W. Heine, R. Peavy, A. J. Durbetaki, J. Org. Chem. 1966, 31, 3924-3927.
24. J. W. Lown, M. H. Akthar, Can. J. Chem. 1972, 50, 2236-2248.
25. H. Duewell, Austr. J. Chem. 1977, 30, 1367-1374.
26. M. Förterer, P. Rademacher, Chem. Ber. 1980, 113, 212-225 and literature cited therein.
27. L. M. Jackman, Dynamic NMR Spectroscopv (L. M. Jackman, F. A. Cotton), Academic Press, New York, 1975, p. 203.
28. H. Kessler, Angew. Chem. 1970, 82, 237-253;
29. Angew. Chem. Int. Ed. Engl. 1970, 9, 219-235.
30. S. van der Werf, T. Olijnsma, J. B. F. N. Engberts, Tetrahedron Lett. 1967, 8, 689-693.
31. S. van der Werf, J. B. F. N. Engberts, Tetrahedron Lett. 1968, 9, 3311-3314.
32. A. E. Lemire, J. C. Thompson, Can. J. Chem. 1975, 53, 3732-3738.
33. B. J. Price, R. V. Smallman, I. O. Sutherland, J. Chem. Soc., Chem. Commun. 1966, 319-320.
34. H.-D. Martin, M. Müller, B. Mayer, H. Haddad, A. Steigel, G. Distefano, A. Modelli, Chem. Ber. 1986, 119, 1613-1626.
35. Data provided by the Southern New England Ultraviolet Co., 55 Conolly Parkway, Hamden, Connecticut, USA 06514.
36. P. S. Engel, Chem. Rev. 1980, 80, 99-150.
37. H. Rau, Angew. Chem. 1973, 85, 248-258:
38. Angew. Chem. Int. Ed. Engl. 1973, 72, 224-234.
39. S. Hünig, K. Peters, M. Schmitt, H. G. von Schnering, Collect. Czech. Chem. Commun. 1988, 53, 2082-2095.
40. [2]) in cooperation with H.-D. Martin and B. Mayer, University of Düsseldorf.
41. Compare: A. Padwa, D. Dean, T. Oine, J. Am. Chem. Soc. 1975, 97, 2822-2829;
42. A. Padwa, L. Hamilton, J. Org. Chem. 1966, 37, 1995-1997.
43. R. Huisgen, W. Scheer, H. Huber, J. Am. Chem. Soc. 1967, 89, 1753-1755;
44. R. Huisgen, W. Scheer, H. Mäder, E. Brunn, Angew. Chem. 1969, 81, 621-623;
45. Angew. Chem. Int. Ed. Engl. 1969, 8, 604-606.
46. A. P. Schaap, G. Prasad, S. Siddiqui, Tetrahedron Lett. 1984, 25, 3035-3038.
47. A. P. Schaap, G. Prasad, S. D. Gagnon, Tetrahedron Lett. 1983, 24, 3047-3050.
48. R. Huisgen, W. Scheer, H. Mäder, Angew. Chem. 1969, 81, 619-621;
49. Angew. Chem. Int. Ed. Engl. 1969, 8, 602-604.
50. E. Brunn, R. Huisgen, Tetrahedron Lett. 1971, 72, 473-476.
51. H. W. Heine, R. Peavy, A. J. Durbetaki, J. Org. Chem. 1966, 31, 3924-3927.
52. J. W. Lown, M. H. Akthar, Can. J. Chem. 1972, 50, 2236-2248.
53. H. Duewell, Austr. J. Chem. 1911, 30, 1367-1374.
54. S. R. Tanny, F. W. Fowler, J. Am. Chem. Soc. 1973, 95, 7320-7324.
55. Th. Golz, S. Hammes, F.-G. Klärner, Chem. Ber. 1993, 126, 485-498.
56. G. Sedelmeier, Ph. D. Thesis, University of Freiburg, 1979;
57. H. Prinzbach, G. Sedelmeier, H.-D. Martin, Angew. Chem. 1977, 89, 111-112;
58. Angew. Chem. Int. Ed. Engl. 1977, 16, 103-104.
59. M. Klaus, H. Prinzbach, Angew. Chem. 1971, 83, 292-293;
60. Angew. Chem. Int. Ed. Engl. 1971, 10, 273-274.
61. K. Umano, H. Koura, H. Inoue, Bull. Chem. Soc. Jpn. 1981, 54, 2827-2828.
62. M. Klaus, K. Prinzbach, Angew. Chem. 1969, 81, 289-291;
63. Angew. Chem. Int. Ed. Engl. 1969, 8, 276-279.
64. W. F. Forbes, R. Shilton, A. Balasubramanian, J. Org. Chem. 1964, 29, 3527-3531.
65. P. S. Engel, D. E. Keys, A. Kitamura, J. Am. Chem. Soc. 1985, 107, 4964-4975.
66. N. J. Turro, Modern Molecular Photochemistry, The Benjamin/ Cummings Publishing Co., Menlo Park, California, 1978, p. 544 and literature cited there.
67. H. Bisle, H. Rau, Chem. Phys. Lett. 1975, 31, 264-266.
68. N. J. Turro, C. A. Renner, W. H. Waddell, T. J. Katz, J. Am. Chem. Soc. 1976, 98, 4320-4322.
69. [8a], p. 90.