Difference in photochemical behavior in 3,6- and 2,5-di-tert-butyl-3H-azepine: The first photochemical bond formation between 2- and 6-position of 3H-azepine ring

Journal of Heterocyclic Chemistry

Volumn 39, Issue 6, 2002, Pages 1337-1338

  Satake, Kyosuke ^a   Takami, Shizuka ^b   Tawada, Yuko ^b   Kimura, Masaru ^b  

^a OKAYAMA UNIVERSITY   (Japan)

^b KYUSHU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

2,5 DI TERT BUTYL 3H AZEPINE; 3,6 DI TERT BUTYL 3H AZEPINE; AZEPINE DERIVATIVE; BICYCLO COMPOUND; PYRIDINE DERIVATIVE; SILICON DIOXIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; CYCLIZATION; FILTER; IRRADIATION; ISOMERISM; NUCLEAR MAGNETIC RESONANCE; PHOTOCHEMISTRY; PHOTOLYSIS;

EID: 0036875179     PISSN: 0022152X     EISSN: None     Source Type: Journal    
DOI: 10.1002/jhet.5570390637     Document Type: Article

References (14)

1. R. A. Odum and B. Schmall, J. Chem. Research (s), 276 (1997); R. A. Odum and B. Schmall, J. Chem. Soc., Chem. Commun., 1209 (1969).
2. R. A. Odum and B. Schmall, J. Chem. Research (s), 276 (1997); R. A. Odum and B. Schmall, J. Chem. Soc., Chem. Commun., 1209 (1969).
3. E. Vogel, H.-J. Altenbach, J.-M. Drossard, H. Schmickler, and H. Stegelmeier, Angew. Chem. Int. Ed. Engl., 13, 1016 (1980).
4. K. Satake, R. Okuda, M. Hashimoto, Y. Fujiwara, I. Watadani, H. Okamoto, M. Kimura, and S. Morosawa, J. Chem. Soc., Chem. Commun., 1154 (1991);
5. K. Satake, R. Okuda, M. Hashimoto, Y. Fujiwara, H. Okamoto, M. Kimura, and S. Morosawa, J. Chem. Soc., Perkin Trans. 1, 1753 (1994).
6. Photoirradiation experiments described on this paper were carried out with a 100 W high-pressure mercury lamp.
7. M. Ogata, H. Matsumoto, and H. Kano, Tetrahedron, 25, 5217 (1969).
8. R. J. Srinivasan, J. Am. Chem. Soc., 84, 3432 (1962); A. P. ter Boorg and H. Kloosterziel, Rec. Trav. Chim., 84, 241 (1965); T. Tezuka, M. Kimura, A. Sato, and T. Mukai, Bull. Chem. Soc. Jpn., 43, 1120 (1970).
9. R. J. Srinivasan, J. Am. Chem. Soc., 84, 3432 (1962); A. P. ter Boorg and H. Kloosterziel, Rec. Trav. Chim., 84, 241 (1965); T. Tezuka, M. Kimura, A. Sato, and T. Mukai, Bull. Chem. Soc. Jpn., 43, 1120 (1970).
10. R. J. Srinivasan, J. Am. Chem. Soc., 84, 3432 (1962); A. P. ter Boorg and H. Kloosterziel, Rec. Trav. Chim., 84, 241 (1965); T. Tezuka, M. Kimura, A. Sato, and T. Mukai, Bull. Chem. Soc. Jpn., 43, 1120 (1970).
11. C. K. Cheung, R. S. Wedinger and W. J. le Noble, J. Org. Chem., 54, 570 (1989).
12. K. Satake, H. Saitoh, M. Kimura, and S. Morosawa, Heterocycles, 38, 769 (1994).
13. +, 0.4%), 190 (12), 163 (28), 107 (62), 57 (100).
14. 3): δ 0.87 (s, 9H), 1.06 (s, 9H), 1.99 (br s, 1H), 2.12 (ddd, J = 17.7, 2.4, and 1.7 Hz, 1H), 2.78 (dd, J = 17.7 and 2.4 Hz, 1H), 3.11 (dd, J = 2.4 and 1.7 Hz, 1H), 3.23 (s, 3H), 4.35 (d, J = 2.4 Hz, 1H), 5.44 (t, J = 2.4 Hz, 1H).