Photoisomerization by Hula twist: 2,2′-Dimethylstilbene and a ring-fused analogue

Angewandte Chemie - International Edition

Volumn 42, Issue 31, 2003, Pages 3630-3633

  Imamoto, Yasushi ^b   Kuroda, Takayuki ^b   Kataoka, Mikio ^b   Shevyakov, Sergey ^a   Krishnamoorthy, G ^a   Liu, Robert S H ^a  

^a UNIVERSITY OF HAWAII   (United States)

^b NARA INSTITUTE OF SCIENCE AND TECHNOLOGY   (Japan)

Author keywords

Alkenes; Isomerization; Photochemistry; Reaction mechanisms

Indexed keywords

CONFORMATIONS; GLASS; SOLID SOLUTIONS; SOLUTIONS;

PHOTOISOMERIZATION;

ISOMERIZATION;

2,2' DIMETHYLSTILBENE; ALKENE DERIVATIVE; STILBENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; CHEMICAL STRUCTURE; CONFORMATION; ISOMERISM; LIQUID; PHOTOCHEMISTRY; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 0042468986     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200351763     Document Type: Article

References (24)

1. a) R. S. H. Liu, G. S. Hammond, Proc. Natl. Acad. Sci. USA 2000, 97, 11153-11158;
2. b) R. S. H. Liu, Acc. Chem. Res. 2001, 34, 555-562;
3. c) R. S. H. Liu, G. S. Hammond, Chem. Eur. J. 2001, 7, 4536-4544.
4. See, for example, a) J. Saltiel, D. F. Sears, Jr., D.-H. Ko, K.-M. Park in CRC Handbook of Organic Photochemistry and Photobiology (Eds.: W. M. Horspool, P.-L. Song), CRC, Boca Raton, 1994, pp. 1-15;
5. b) W. J. Leigh in CRC Handbook of Organic Photochemistry and Photobiology (Eds.: W. M. Horspool, P.-L. Song), CRC Press, Boca Raton, 1994, pp. 123-142;
6. c) H. J. C. Jacobs, W. H. Laarhoven in CRC Handbook of Organic Photochemistry and Photobiology (Eds.: W. M. Horspool, P.-L. Song), CRC, Boca Raton, 1994, pp. 143-154.
7. a) R. S. H. Liu, A. E. Asato, Proc. Natl. Acad. Sci. USA 1985, 82, 259-263;
8. b) R. S. H. Liu, D. T. Browne Acc. Chem. Res. 1986, 19, 42-48.
9. For selected papers on the photoisomerization pathways, torsional relaxation, and the Hula twist, see a) R. S. H. Liu, Photochem. Photobiol. 2002, 76, 580-583; b) M. Uda, T. Mizutani, J. Hayakawa, A. Momotake, M. Ikegami, R. Nagahata, T. Arai, Photochem. Photobiol. 2002, 76, 596-605; c) S. Wilsey, K. N. Houk, Photochem. Photobiol. 2002, 76, 616-621; d) M. Squillacote, T. Semple, J.-W. Chen, F. Liang, Photochem. Photobiol. 2002, 76, 634-639.
10. For selected papers on the photoisomerization pathways, torsional relaxation, and the Hula twist, see a) R. S. H. Liu, Photochem. Photobiol. 2002, 76, 580-583; b) M. Uda, T. Mizutani, J. Hayakawa, A. Momotake, M. Ikegami, R. Nagahata, T. Arai, Photochem. Photobiol. 2002, 76, 596-605; c) S. Wilsey, K. N. Houk, Photochem. Photobiol. 2002, 76, 616-621; d) M. Squillacote, T. Semple, J.-W. Chen, F. Liang, Photochem. Photobiol. 2002, 76, 634-639.
11. For selected papers on the photoisomerization pathways, torsional relaxation, and the Hula twist, see a) R. S. H. Liu, Photochem. Photobiol. 2002, 76, 580-583; b) M. Uda, T. Mizutani, J. Hayakawa, A. Momotake, M. Ikegami, R. Nagahata, T. Arai, Photochem. Photobiol. 2002, 76, 596-605; c) S. Wilsey, K. N. Houk, Photochem. Photobiol. 2002, 76, 616-621; d) M. Squillacote, T. Semple, J.-W. Chen, F. Liang, Photochem. Photobiol. 2002, 76, 634-639.
12. For selected papers on the photoisomerization pathways, torsional relaxation, and the Hula twist, see a) R. S. H. Liu, Photochem. Photobiol. 2002, 76, 580-583; b) M. Uda, T. Mizutani, J. Hayakawa, A. Momotake, M. Ikegami, R. Nagahata, T. Arai, Photochem. Photobiol. 2002, 76, 596-605; c) S. Wilsey, K. N. Houk, Photochem. Photobiol. 2002, 76, 616-621; d) M. Squillacote, T. Semple, J.-W. Chen, F. Liang, Photochem. Photobiol. 2002, 76, 634-639.
13. A. M. Muller, S. Lochbrunner, W. E. Schmid, W. Fuss, Angew. Chem. 1998, 110, 520-522; Angew. Chem. Int. Ed. 1998, 37, 505-507.
14. A. M. Muller, S. Lochbrunner, W. E. Schmid, W. Fuss, Angew. Chem. 1998, 110, 520-522; Angew. Chem. Int. Ed. 1998, 37, 505-507.
15. -1. As expected, the Z isomer has a shorter retention time than the E isomer on silica gel.
16. T. Yoshizawa, Y. Shichida, Methods Enzymol. 1982, 81, 333-354.
17. U. Mazzucato, F. Momicchioli, Chem. Rev. 1991, 91, 1679-1719.
18. Calculations were performed by Drs. Manoharan and Alabugin by using B3LYP6-31G* the density functional (DFT) method.
19. The actinometer system (trans-stilbene, φ = 0.49) was run at room temperature, see J. Saltiel, A. Marinari, D. W.-L. Chang, J. C. Mitchener, E. D. Megarity, J. Am. Chem. Soc. 1979, 101, 2982-2996.
20. M. E. Squillacote, R. S. Sheridan, O. L. Chapman, F. A. L. Anet, J. Am. Chem. Soc. 1979, 101, 3657-3659.
21. J. R. Ackerman, S. A. Forman, M. Hussain, B. Kohler, J. Chem. Phys. 1984, 80, 39-44.
22. a) M. V. Alfimov, V. F. Razumov, A. G. Rachinsky, V. N. Lisvan, Yu. B. Scheck, Chem. Phys. Lett. 1983, 101, 593-597;
23. b) N. Castel, E. Fischer, J. Mol. Struct. 1985, 127, 159-166.
24. D. Sempedro Ruiz, A. Cembran, M. Garavelli, M. Olivucci, W. Fuss, Photochem. Photobiol. 2002, 76, 622-633.