Photochemical ring opening of 7-benzoyl-and 7-methoxycarbonyldibenzonorcaradienes. Competing 1,2-hydrogen shift and cyclization reactions of 1,3-diradicals

Organic Letters

Volumn 3, Issue 12, 2001, Pages 1885-1888

  Bogdanova, Aneta ^a   Popik, Vladimir V ^a  

^a BOWLING GREEN STATE UNIVERSITY   (United States)

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ARTICLE;

EID: 0041906578     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol015938r     Document Type: Article

References (29)

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2. (b) R = Cl, R′ = Alk: Robert, M.; Likhotvorik, I.; Platz, M. S.; Abbot, S. C.; Kirchoff, M. M.; Johnson, R. J. Phys. Chem. A 1998, 102, 1507.
3. (c) R, R′ = Cl: Chateauneuf, J. E.; Johnson, R. P.; Kirchhoff, M. M. J. Am. Chem. Soc. 1990, 112, 3217.
4. (d) R, R′ = H: Richardson, D. B.; Durret, L. R.; Martin, J. M., Jr.; Putman, N. E.; Slaymaker, S. C.; Dvoretzky, I. J. Am. Chem. Soc. 1965, 87, 2763.
5. (e) R = H, R′ = t-Bu: Click, H. C.; Likhtvorik, I. R.; Jones, M., Jr. Tetrahedron Lett. 1995, 36, 5715.
6. (f) R. R′ = Alk: Lewis, S. M.; Hernandez, S.; Abbot, S. C; Kirchhoff, M. M.; Johnson, R. P. Abstracts of Papers, 220th Meeting of the American Chemical Society; American Chemical Society: Washington, DC, 2000; ORGN-372.
7. (a) For example: Moreau, W. M. Semiconductor Lithography; Plenum Press: New York, 1988. Reiser, A. Photoreactive Polymers: The Science and Technology of Resists; Wiley: New York, 1989. Reichmanis, E.; Thompson, L. F. Chem. Rev. 1989, 89, 1273.
8. (a) For example: Moreau, W. M. Semiconductor Lithography; Plenum Press: New York, 1988. Reiser, A. Photoreactive Polymers: The Science and Technology of Resists; Wiley: New York, 1989. Reichmanis, E.; Thompson, L. F. Chem. Rev. 1989, 89, 1273.
9. (a) For example: Moreau, W. M. Semiconductor Lithography; Plenum Press: New York, 1988. Reiser, A. Photoreactive Polymers: The Science and Technology of Resists; Wiley: New York, 1989. Reichmanis, E.; Thompson, L. F. Chem. Rev. 1989, 89, 1273.
10. (b) Yang, Y.; Huang, S.; He, H.; Mau, A. W. H.; Dai, L. J. Am. Chem. Soc. 1999, 121, 10832.
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13. Likhotvorik, I.; Zhu, Z.; Tae, E. L.; Tippmann, E.; Platz, M. S. J. Am. Chem. Soc. 2001, 123, in press.
14. The preparation procedures for the compounds of 1a, 1b, and 1c, the spectral data for these compounds, and details of photolyses of 1a, 1b, and 1c are provided in the Supporting Information.
15. Guziec, F. S.; Luzzio, F. A. J. Org. Chem. 1983, 48, 2434. Castellino, A. J.; Bruice, T. C. J. Am. Chem. Soc. 1988, 110, 7512.
16. Guziec, F. S.; Luzzio, F. A. J. Org. Chem. 1983, 48, 2434. Castellino, A. J.; Bruice, T. C. J. Am. Chem. Soc. 1988, 110, 7512.
17. De Feyter, S.; Diau, E. W.-G.; Scala, A. A.; Zewail, A. H. Chem. Phys. Lett. 1999, 303, 249. Doubleday, C.; Bolton, K.; Peslherbe, G. H.; Hase, W. L. J. Am. Chem. Soc. 1996, 118, 9922.
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23. Time-resolve experiments were conducted using both Q-switched Nd:YAG (Serguievski, P.; Ford, W.E.; Rodgers, M. A. J. Langmuir 1996, 12, 348) and excimer (Andraos, J.; Chiang, Y.; Huang, G.-C.; Kresge, A. J.; Scaiano, J. C. J. Am. Chem. Soc. 1993, 115, 10605) laser systems.
24. Time-resolve experiments were conducted using both Q-switched Nd:YAG (Serguievski, P.; Ford, W.E.; Rodgers, M. A. J. Langmuir 1996, 12, 348) and excimer (Andraos, J.; Chiang, Y.; Huang, G.-C.; Kresge, A. J.; Scaiano, J. C. J. Am. Chem. Soc. 1993, 115, 10605) laser systems.
25. UV spectra of starting materials and products can be found in the Supporting Information.
26. Johnson, W. T. G.; Hrovat, D. A.; Borden, W. T. J. Am. Chem. Soc. 1999, 121, 7766. Bergman, R. G.; Carter, W. L. J. Am. Chem. Soc. 1969, 91, 7411.
27. Johnson, W. T. G.; Hrovat, D. A.; Borden, W. T. J. Am. Chem. Soc. 1999, 121, 7766. Bergman, R. G.; Carter, W. L. J. Am. Chem. Soc. 1969, 91, 7411.
28. Semiempirical calculation were performed using the Spartan Pro program (Wavefuction, Inc.) at the PM3 level.
29. Xe-flash lamp system is described in Chiang, Y.; Hojatti, M.; Keeffe, J. R.; Kresge, A. J.; Schepp, N. P.; Wirz, J. J. Am. Chem. Soc. 1987, 109, 4000.