Stereodifferentiation in the photochemical cycloreversion of diastereomeric methoxynaphthalene - oxetane dyads

Journal of Organic Chemistry

Volumn 70, Issue 4, 2005, Pages 1376-1381

  Pérez Ruiz, Raúl ^a   Gil, Salvador ^b   Miranda, Miguel A ^a  

^a CSIC   (Spain)

^b UNIVERSITY OF VALENCIA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ACETONITRILE; CONFORMATIONS; ELECTRON TRANSITIONS; FLUORESCENCE; PHOTOCHEMICAL REACTIONS; PHOTOREACTIVITY; SOLVENTS;

CHLOROFORM; OXETANE; PHOTOCHEMICAL CYCLOREVERSION; STEREODIFFERENTIATION;

NAPHTHALENE;

ACETONITRILE; CHLOROFORM; CYCLOBUTANE; DEOXYRIBODIPYRIMIDINE PHOTOLYASE; METHOXYNAPHTHALENE; NAPHTHALENE DERIVATIVE; OXETANE DERIVATIVE; PYRIMIDINE DIMER; UNCLASSIFIED DRUG;

ABSORPTION SPECTROSCOPY; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; DIASTEREOISOMER; DNA DAMAGE; ELECTRON TRANSPORT; FLUORESCENCE SPECTROSCOPY; NUCLEAR OVERHAUSER EFFECT; PHOTOLYSIS; PROTON NUCLEAR MAGNETIC RESONANCE; STEADY STATE; STEREOCHEMISTRY; ULTRAVIOLET IRRADIATION; ULTRAVIOLET SPECTROSCOPY;

EID: 13844308310     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo048708+     Document Type: Article

References (23)

1. Taylor, J.-S. J. Chem. Educ. 1990, 67, 835-841.
2. Taylor, J.-S. Acc. Chem. Res. 1994, 27, 76-82.
3. Heelis, P. F.; Hartman, B. F.; Rose, S. D. Chem. Soc. Rev. 1995, 289-297.
4. Smith, C. A.; Wang, M.; Jiang, N.; Che, L.; Zhao, X.; Taylor, J.-S. Biochemistry 1996, 35, 4146-4154.
5. Taylor, J.-S.; Nadji, S. Tetrahedron 1991, 47, 2579-2590.
6. Kim, S.-T.; Malhorta, K.; Smith, C. A.; Taylor, J.-S.; Sancar, A. J. Biol. Chem. 1994, 269, 8535-8540.
7. Kim, S.-T.; Malhotra, K.; Smith, C. A.; Taylor, J. S.; Sancar, A. Photochem. Photobiol. 1996, 63, 292-295.
8. Hitomi, K.; Nakamura, H.; Kim, S.-T.; Mizukoshi, T.; Ishikawa, T.; Iwai, S.; Todo, T. J. Biol. Chem. 2001, 276, 10103-10109.
9. Cichon, M. K.; Arnold, S.; Carell, T. Angew. Chem., Int. Ed. Engl. 2002, 41, 767-770. Sancar, A. Chem. Rev. 2003, 103, 2203-2237.
10. Cichon, M. K.; Arnold, S.; Carell, T. Angew. Chem., Int. Ed. Engl. 2002, 41, 767-770. Sancar, A. Chem. Rev. 2003, 103, 2203-2237.
11. Epple, B.; Wallenbom, E.-U.; Carell, T. J. Am. Chem. Soc. 1997, 119, 7440-7451.
12. Hartman, R. F.; Rose, S. D. J. Am. Chem. Soc. 1992, 114, 3559-3560.
13. Prakash, G.; Falvey, D. E. J. Am. Chem. Soc. 1995, 117, 11375-11376.
14. Joseph, A.; Prakash, G.; Falvey, D. E. J. Am. Chem. Soc. 2000, 122, 11219-11225.
15. Joseph, A.; Falvey, D. E. J. Am. Chem. Soc. 2001, 123, 3145-3146.
16. Joseph, A.; Falvey, D. E. Photochem. Photobiol. Sci. 2002, 1, 632-635.
17. Pérez-Ruiz, R.; Izquierdo, M. A.; Miranda, M. A. J. Org. Chem. 2003, 68, 10103-10108.
18. (a) Martinez, L. J.; Scaiano, J. C. Photochem. Photobiol. 1998, 68, 646-651,
19. (b) Moore, D. E.; Chappuis, P. P. Photochem. Photobiol. 1988, 47, 173-180.
20. Weller, A. Z. Phys. Chem. (Muenchen) 1982, 133, 93-98.
21. (a) Boscá, F.; Martinez-Máñez, R.; Miranda, M. A.; Primo, J.; Soto, J.; Vañó, L. J. Pharm. Sci. 1992, 81, 479-482.
22. (b) Boscá, F.; Marín, M. L.; Miranda, M. A. Photochem. Photobiol. 2001, 74, 637-655.
23. Murov, S. L.; Carmichael, I.; Hug, G. L. Handbook of Photochemistry, 2nd ed.; Marcel Dekker: New York, 1993; p 284.