Photochemical reactions of chloranil with cyclooctene, 1,5-cyclooctadiene, and cyclohexene revisited

European Journal of Organic Chemistry

Volumn , Issue 5, 2011, Pages 968-982

  Christl, Manfred ^a   Braun, Max ^a   Deeg, Oliver ^a   Wolff, Stephan ^a  

^a UNIVERSITY OF WÜRZBURG   (Germany)

Author keywords

Cycloaddition; Dechlorination; Endiones; Photochemistry; Polycycles

Indexed keywords

EID: 79551509356     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.201001304     Document Type: Article

References (36)

1. K. Maruyama, A. Osuka in The Chemistry of Quinonoid Compounds (Eds.:, S. Patai, Z. Rappoport), Wiley, New York, 1988, vol. 2, part 1, chapter13.
2. D. Creed in CRC Handbook of Organic Photochemistry and Photobiology (Eds.:, W. M. Horspool, P.-S. Song), CRC Press, Boca Raton, 1995, pp. 737-747.
3. A. Gilbert in CRC Handbook of Organic Photochemistry and Photobiology, 2nd ed. (Eds.:, W. M. Horspool, F. Lenci), CRC Press, Boca Raton, 2004, chapter 87.
4. S. M. Hubig, T. M. Bockman, J. K. Kochi, J. Am. Chem. Soc. 1997, 119, 2926-2935.
5. D. Rehm, A. Weller, Isr. J. Chem. 1970, 8, 259-271.
6. A. Weller, Z. Phys. Chem. (Wiesbaden) 1982, 133, 93-98.
7. J.-H. Xu, Y.-L. Song, Z.-G. Zhang, L.-C. Wang, J.-W. Xu, Tetrahedron 1994, 50, 1199-1210.
8. P. M. Rentzepis, D. W. Steyert, H. D. Roth, C. J. Abelt, J. Phys. Chem. 1985, 89, 3955-3960.
9. J.-H. Xu, L.-C. Wang, J.-W. Xu, B.-Z. Yan, H.-C. Yuan, J. Chem. Soc. Perkin Trans. 1 1994, 571-577.
10. M. Christl, M. Braun, Angew. Chem. 1989, 101, 636-638; Angew. Chem. Int. Ed. Engl. 1989, 28, 601 -603.
11. M. Braun, M. Christl, O. Deeg, M. Rudolph, E.-M. Peters, K. Peters, Eur. J. Org. Chem. 1999, 2093-2101.
12. G. O. Schenck, E. K. von Gustorf, B. Kim, G. v. Bünau, G. Pfundt, Angew. Chem. 1962, 74, 510-511; Angew. Chem. Int. Ed. Engl. 1962, 1, 516.
13. G. Jones II, W. A. Heany, J. Phys. Chem. 1986, 90, 5410-5414.
14. M. Braun, Dissertation, University of Würzburg, 1990.
15. J. A. Barltrop, B. Hesp, J. Chem. Soc. C 1967, 1625-1635.
16. J. Xue, J.-W. Xu, L. Yang, J.-H. Xu, J. Org. Chem. 2000, 65, 30-40.
17. M. Braun, M. Christl, E.-M. Peters, K. Peters, J. Chem. Soc. Perkin Trans. 1 1999, 2813-2820.
18. D. Bryce-Smith, A. Gilbert, Tetrahedron Lett. 1964, 5, 3471-3473.
19. S. S. Kim, D. Y. Yoo, I. H. Cho, S. C. Shim, Bull. Korean Chem. Soc. 1987, 8, 296-298.
20. Handbook of Tables for Organic Compound Identification, 3rd ed., CRC Press, Cleveland, 1967, p. 126.
21. T. Shono, A. Ikeda, J. Hayashi, S. Hakozaki, J. Am. Chem. Soc. 1975, 97, 4261-4264.
22. K. Peters, E.-M. Peters, M. Braun, S. Wolff, M. Christl, Z. Kristallogr.-New Cryst. Struct. 2000, 215, 45-46.
23. A. R. Pinder, Synthesis 1980, 425-452.
24. K. Schaffner, Pure Appl. Chem. 1968, 16, 75-85.
25. N. J. Turro, Modern Molecular Photochemistry, Benjamin, Menlo Park, 1978, pp. 559-560.
26. A. P. Avdeenko, A. L. Yusina, Zh. Org. Khim. 1995, 31, 458-461; Russ. J. Org. Chem. (Engl. Transl.) 1995, 31, 418 -421.
27. W. M. Horspool, Photochemistry 1997, 28, 341-378.
28. G. I. Fray, R. G. Saxton, The Chemistry of Cyclooctatetraene and Its Derivatives, Cambridge University Press, Cambridge, 1978, p. 7.
29. P. Metzger, C. Cabestaing, E. Casadevall, A. Casadevall, Org. Magn. Reson. 1982, 19, 144-147.
30. J.-L. Mieusset, U. H. Brinker, J. Org. Chem. 2007, 72, 10211-10219.
31. P. G. Gassman, R. Yamaguchi, G. F. Koser, J. Org. Chem. 1978, 43, 4392-4393.
32. C. Batich, O. Ermer, E. Heilbronner, J. R. Wiseman, Angew. Chem. 1973, 85, 302-303; Angew. Chem. Int. Ed. Engl. 1973, 12, 312 -314.
33. [29] for that of norbornene).
34. S. W. Benson, Thermochemical Kinetics, 2nd ed., Wiley, New York, 1976, p. 273.
35. Y. Inoue, N. Yamasaki, A. Tai, D. Akira, Y. Daino, T. Yamada, T. Hakushi, J. Chem. Soc. Perkin Trans. 2 1990, 1389-1394.
36. Y. Inoue, H. Tsuneishi, T. Hakushi, A. Tai in Photochemical Key Steps in Organic Synthesis-An Experimental Course Book (Eds.:, J. Mattay, A. Griesbeck), VCH, Weinheim, 1994, p. 207.