Synthesis of 1,2,3-Tri-t-butyl-6,13- and 8,9,10-Tri-t-butyl-5,14-pentacenequinones and their photochromic behaviors : New photochromic molecules

Tetrahedron

Volumn 52, Issue 12, 1996, Pages 4269-4276

  Miki, Sadao ^a   Ito, Jun ^a   Noda, Ryuki ^a   Nishijima, Nariaki ^a   Fukunishi, Koushi ^a  

^a KYOTO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

POLYCYCLIC AROMATIC HYDROCARBON; QUINONE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; PHOTOCHEMISTRY; PRIORITY JOURNAL; SPECTROPHOTOMETRY;

EID: 0030007917     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00087-7     Document Type: Article

References (18)

1. a) Darcy, P. J. ; Heller, H. G. ; Strydam, P. J. ; Whitall, J., J. Chem. Soc., Perkin Trans I, 1981, 202 ;
2. b) Irie, M.; M. Mohn, M., J. Org. Chem., 1988, 53, 803., Irie, M.; Miyatake, ; Uchida, K.; Eriguchi, T., J. Am. Chem. Soc., 1994, 116, 9894 and references cited therein.
3. b) Irie, M.; M. Mohn, M., J. Org. Chem., 1988, 53, 803., Irie, M.; Miyatake, ; Uchida, K.; Eriguchi, T., J. Am. Chem. Soc., 1994, 116, 9894 and references cited therein.
4. a) Yoshida, Z., Jpn Kokai Tokkyo Koho, JP 138349 (1979) ;
5. b) Miki, S.; Ema, T.; Shimizu, R.; Yoshida, Z., Tetrahedron Lett., 1992, 33, 1619 .
6. c) Yoshida, Z.; Miki, S.; Matsuo, K.; Shiojiri, E., Jpn Kokai Tokkyo Koho, JP 01238546 (1989)
7. d) El-Shishtawy, R. M.; Fukunishi, K.; Miki, S., Tetrahedron Lett., 1995, 36, 3177.
8. a) Miki, S.; Matsuo, K.; Yoshida, M.; Yoshida, Z., Tetrahedron Lett., 1988, 29, 2211.
9. b) Miki, S.; Kagawa, H.; Matsuo, K.; Kobayashi, O.; Yoshida, M.; Yoshida, Z., Tetahedron, 1992, 48, 1567.
10. c) Nakayama, T.; Yamaguchi, T.; Ushida, K.; Hamanoue, K.; Miki, S.; Matsuo, K.; Yoshida, Z., Chem. Phys. Lett., 1988, 148, 259 .
11. Maier, G.; Pfriem, S., Chem. Ber., 1981, 114, 3965.
12. Cava, M. P.; Deana, A. A.; Muth, K., J. Am. Chem. Soc.,1959, 81, 6458.
13. Zander, M., Ber. Bunsen. Physk. Chem., 1967, 71, 424 .
14. Katz, T. J.; Wang, E. J.; Acton, N., J. Am. Chem. Soc., 1971, 93, 3782.
15. Murov, S. L., Handbook of Photochemistry, Marcel Dekker INC.,New York, 1973
16. Horspool, W. H., Synthetic Organic Photochemistry", Plenum Press, New York, 1984); pp. 507-508.
17. Heller, H .G.; Langan, J. R., J. Chem. Soc., Perkin II, 1981, 341.
18. 1NMR for methylene protons of each bromomethyl group appeared as AB quartet probably due to the magnetic diastereotopics caused by a large out-of-plane deformation of the aromatic ring substituted with the t-butyl groups.