Retro-Diels-Alder femtosecond reaction dynamics

Journal of the American Chemical Society

Volumn 118, Issue 36, 1996, Pages 8755-8756

  Horn, B A ^a   Herek, J L ^a   Zewail, A H ^a  

^a CALIFORNIA INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

NORBORNANE DERIVATIVE;

ARTICLE; CHEMICAL REACTION KINETICS; MASS SPECTROMETRY; MOLECULAR DYNAMICS;

EID: 0029842755     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9620696     Document Type: Article

References (40)

1. Diels, O.; Alder, K. Justus Liebigs Ann. Chem. 1928, 460, 98. Diels, O.; Alder, K. Ber. 1929, 62, 554.
2. Diels, O.; Alder, K. Justus Liebigs Ann. Chem. 1928, 460, 98. Diels, O.; Alder, K. Ber. 1929, 62, 554.
3. For an excellent review, see: Houk, K. N.; Li, Y.; Evanseck, J. D. Angew. Chem., Int. Ed. Engl. 1992, 31, 682.
4. Dewar, M. J. S.; Jie, C. Acc. Chem Res. 1992, 25, 537-543.
5. Evans, M. G.; Warhurst, E. Trans. Faraday Soc. 1938, 34, 614. Evans, M. G. Trans. Faraday Soc. 1939, 35, 824.
6. Evans, M. G.; Warhurst, E. Trans. Faraday Soc. 1938, 34, 614. Evans, M. G. Trans. Faraday Soc. 1939, 35, 824.
7. Eyring, H.; Polanyi, M. Z. Phys. Chem. 1931, 279. Evans, M. G.; Polanyi, M. G. Trans. Faraday Soc. 1938, 34, 11.
8. Eyring, H.; Polanyi, M. Z. Phys. Chem. 1931, 279. Evans, M. G.; Polanyi, M. G. Trans. Faraday Soc. 1938, 34, 11.
9. Woodward, R. B.; Hoffmann, R. The Conservation of Orbital Symmetry, Academic Press: New York, 1970.
10. Fukui, K. Tetrahedron Lett. 1965, 2009. Fukui, K. Acc. Chem Res. 1971, 4, 57.
11. Fukui, K. Tetrahedron Lett. 1965, 2009. Fukui, K. Acc. Chem Res. 1971, 4, 57.
12. Woodward, R. B.; Katz, T. J. Tetrahedron 1959, 5, 70.
13. Berson, J. A.; Remanick, A.; Mueller, W. A. J. Am. Chem. Soc. 1960, 82, 5501-5502. Berson, J. A.; Remanick, A. J. Am. Chem. Soc. 1961, 83, 4947-4956.
14. Berson, J. A.; Remanick, A.; Mueller, W. A. J. Am. Chem. Soc. 1960, 82, 5501-5502. Berson, J. A.; Remanick, A. J. Am. Chem. Soc. 1961, 83, 4947-4956.
15. Dewar, M. J. S. Tetrahedron Lett. 1959, 16.
16. Lambert, J. B.; Roberts, J. D. Tetrahedron Lett. 1965, 1457.
17. Kim, S. K.; Pedersen, S.; Zewail, A. H. J. Chem. Phys. 1995, 103, 477-480.
18. Pedersen, S.; Herek, J. L.; Zewail, A. H. Science 1994, 266, 1359-1364.
19. Owens, K. A.; Berson, J. A. J. Am. Chem. Soc. 1990, 112, 5973. Wessel, T. E.; Berson, J. A. J. Am. Chem. Soc. 1994, 116, 495.
20. Owens, K. A.; Berson, J. A. J. Am. Chem. Soc. 1990, 112, 5973. Wessel, T. E.; Berson, J. A. J. Am. Chem. Soc. 1994, 116, 495.
21. Zewail, A. H. Femtochemistry: Ultrafast Dynamics of the Chemical Bond; World Scientific: Singapore, 1994, and references therein.
22. Herndon, W. C.; Cooper, W. B.; Chambers, M. J. J . Chem Phys 1964, 68, 2016-2018. Roquitte, B. C. J. Phys. Chem. 1965, 69, 1351-1354. Salazar, J.; Marquez, M.; Barriola, A. Acta Cient. Venez. 1987, 38, 505-506. Woods, W. G. J. Org. Chem. 1958, 23, 110-112. Birely, J. H.; Chesick, J. P. J. Phys. Chem. 1962, 66, 568-570.
23. Herndon, W. C.; Cooper, W. B.; Chambers, M. J. J . Chem Phys 1964, 68, 2016-2018. Roquitte, B. C. J. Phys. Chem. 1965, 69, 1351-1354. Salazar, J.; Marquez, M.; Barriola, A. Acta Cient. Venez. 1987, 38, 505-506. Woods, W. G. J. Org. Chem. 1958, 23, 110-112. Birely, J. H.; Chesick, J. P. J. Phys. Chem. 1962, 66, 568-570.
24. Herndon, W. C.; Cooper, W. B.; Chambers, M. J. J . Chem Phys 1964, 68, 2016-2018. Roquitte, B. C. J. Phys. Chem. 1965, 69, 1351-1354. Salazar, J.; Marquez, M.; Barriola, A. Acta Cient. Venez. 1987, 38, 505-506. Woods, W. G. J. Org. Chem. 1958, 23, 110-112. Birely, J. H.; Chesick, J. P. J. Phys. Chem. 1962, 66, 568-570.
25. Herndon, W. C.; Cooper, W. B.; Chambers, M. J. J . Chem Phys 1964, 68, 2016-2018. Roquitte, B. C. J. Phys. Chem. 1965, 69, 1351-1354. Salazar, J.; Marquez, M.; Barriola, A. Acta Cient. Venez. 1987, 38, 505-506. Woods, W. G. J. Org. Chem. 1958, 23, 110-112. Birely, J. H.; Chesick, J. P. J. Phys. Chem. 1962, 66, 568-570.
26. Herndon, W. C.; Cooper, W. B.; Chambers, M. J. J . Chem Phys 1964, 68, 2016-2018. Roquitte, B. C. J. Phys. Chem. 1965, 69, 1351-1354. Salazar, J.; Marquez, M.; Barriola, A. Acta Cient. Venez. 1987, 38, 505-506. Woods, W. G. J. Org. Chem. 1958, 23, 110-112. Birely, J. H.; Chesick, J. P. J. Phys. Chem. 1962, 66, 568-570.
27. Roquitte, B. C. J. Phys. Chem. 1965, 69, 2475-2477.
28. Kiefer, J. H.; Kumaran, S. S.; Sundaram, S. J. Chem. Phys. 1993. 99, 3531-3541. Barker, J. R.; King, K. D. J. Chem. Phys. 1995, 103, 4953-4966.
29. Kiefer, J. H.; Kumaran, S. S.; Sundaram, S. J. Chem. Phys. 1993. 99, 3531-3541. Barker, J. R.; King, K. D. J. Chem. Phys. 1995, 103, 4953-4966.
30. Zhao, X.; Continetti, R. E.; Yokoyama, A.; Hintsa, E. J.; Lee, Y. T. J. Chem. Phys. 1989, 91, 4118-4127.
31. The initial two-photon energy is 184 kcal/mol. Because the bond energy is ∼44 kcal/mol, the available energy is ∼140 kcal/mol.
32. -1.
33. Dantus, M.; Bowman, R. M.; Gruebele, M.; Zewail, A. H. J. Chem. Phys. 1989, 91, 7437.
34. Douhal, A.; Kim, S. K.; Zewail, A. H. Nature 1995, 378, 260-263.
35. 26
36. Michl, J.; Bonacic-Koutecky, V. Electronic Aspects of Organic Photochemistry; Wiley: New York, 1990.
37. McDiarmid, R.; Sabljic, A. J. Phys. Chem. 1991, 95, 6455. Yi, W.; Chattopadhyay, A.; Bersohn, R J. Chem. Phys. 1991, 94, 5994.
38. McDiarmid, R.; Sabljic, A. J. Phys. Chem. 1991, 95, 6455. Yi, W.; Chattopadhyay, A.; Bersohn, R J. Chem. Phys. 1991, 94, 5994.
39. Kwart, H.; King, K. Chem. Rev. 1968, 68, 415-447.
40. Roos, B. O.; Merchan, M.; McDiarmid, R.; Xing, X. J. Am. Chem. Soc. 1994, 116, 5927-5936.