Medium- and Substituent-Directed Stereoselective Photoisomerization of Polyenes in the Vitamin A Series. Application of the Dellinger-Kasha Model

Journal of the American Chemical Society

Volumn 105, Issue 14, 1983, Pages 4829-4830

  Liu, R S H ^a   Asato, A E ^a   Denny, M ^a  

^a UNIVERSITY OF HAWAII   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000523857     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00352a048     Document Type: Article

References (17)

1. Photochemistry of Polyenes. 20. For the previous paper in the series, see ref 3c.
2. (a) Brown, P. K.; Wald, G. J. Biol. Chem. 1965, 222, 865-877. (b) Denny, M.; Liu, R. S. H. J. Am. Chem. Soc. 1977, 99, 4865-4867. (c) Tsukida, K.; Kodama, A.; Ito, M. J. Chromatogr. 1977, 134, 331-336. (d) Denny, M.; Chun, M.; Liu, R. S. H. Photochem. Photobiol. 1981, 33, 267-269.
3. (a) Kropf, A.; Hubbard, R. Photochem. Photobiol. 1970, 12, 249-260. (b) Liu, R. S. H.; Denny, M.; Asato, A. E.; Grodowski, M. Nouv. J. Chim. 1979, 3, 503-505. (c) Ramamurthy, V.; Denny, M.; Liu, R. S. H. Tetrahedron Lett. 1981, 22, 2463-2466. (d) Waddell, W. H.; Hopkins, D. L. J. Am. Chem. Soc. 1977, 99, 6457-6459. (e) Waddell, W. H.; Chibara, K. J. Am. Chem. Soc. 1981, 103, 7389-7390.
4. Halley, B. A.; Nelson, E. C. Int. J. Vit. Nutr. Res. 1979, 49, 347-351.
5. Matsumoto, H.; Asato, A. E.; Denny, M.; Baretz, B.; Yen, Y.-P.; Tong, D.; Liu, R. S. H. Biochemistry 1980, 19, 4589-4594.
6. (a) Ramamurthy, V.; Tustin, G.; Yau, C. C.; Liu, R. S. H. Tetrahedron 1975, 31, 193-199. (b) Ramamurthy, V.; Liu, R. S. H. J. Am. Chem. Soc. 1974, 96, 5625-5627.
7. Asato, A. E.; Liu, R. S. H. J. Am. Chem. Soc. 1975, 97, 4128-4130.
8. Miller, D.; Trammell, M.; Kini, A.; Liu, R. S. H. Tetrahedron Lett. 1981, 22, 409-412.
9. Synthesized according to the procedure of Cainelli et al.: Cainelli, G.; Cardillo, G.; Contento, M.; Grasselli, P.; Umani Ronchi, A. Gazz. Chim. Ital. 1973, 103, 117-125.
10. Prepared via Diels-Alder addition of vitamin A acetate with phenyltriazolinone.
11. (a) Dellinger, B.; Kasha, M. Chem. Phys. Lett. 1975, 36, 410-415. (b) Dellinger, B.; Kasha, M. Chem. Phys. Lett. 1976, 38, 9-14. (c) Kasha, M.; Dellinger, B.; Brown, C. In “Bioluminescence and Chemiluminescence”; DeLuca, M. A., McElroy, W. D., Eds.; Academic Press: 1981; pp. 3-16.
12. Unpublished results of V. Ramamurthy and R. S. H. Liu; see also ref 3c.
13. A referee expressed a legitimate concern of the applicability of such kinetic arguments to the longer lived triplets. We wish to add that while equilibration of isomeric triplets has been well established in linear dienes (Saltiel, J.; Rousseau, A. D.; Sykes, A. J. Am. Chem. Soc. 1972, 94, 5903-5905) and linear trienes, 14a evidence does not support such a process in compounds in the vitamin A series. For example, two-bond isomerized products are generally of negligible importance (ref 12 and Waddell, W. H.; Crouch, R.; Nakanishi, K.; Turro, N. J. J. Am. Chem. Soc. 1976, 98, 4189-4192). The absence of secondary quenching effect (Ramamurthy, V.; Liu, R. S. H. J. Am. Chem. Soc. 1976, 98, 2935-2942) further suggests that planar triplets are likely to be much higher in energy than the perpendicular triplets.
14. (a) Liu, R. S. H.; Butt, Y. C. C. J. Am. Chem. Soc. 1971, 93, 1532-1534. (b) Butt, Y. C. C.; Singh, A.; Baretz, B.; Liu, R. S. H. J. Phys. Chem. 1981, 85, 2091-2097.
15. (a) Courtot, P.; Rumin, R.; Salaün, J. Recl. Trav. Chim. Pays-Bas 1979, 98, 192-201. (b) Courtot, P.; Salaün, J. Tetrahedron Lett. 1979, 20, 1851-1854.
16. (a) Zechmeister, L. J. Am. Chem. Soc. 1954, 76, 2308-2313. (b) Baretz, B.; Singh, A.; Liu, R. S. H. Nouv. J. Chim. 1981, 5, 297-303.
17. (a) Sharafy, S.; Muszkat, K. A. J. Am. Chem. Soc. 1971, 93, 4119-4125. (b) See: Saltiel, J.; Charlton, J. L. In “Rearrangements in Ground and Excited States”; deMayo, P., Ed.; Academic Press: New York, 1980; Vol. 3, pp. 25-89.