Thermal Decomposition of Chroman. Reactivity of o-Quinone Methide

Journal of Organic Chemistry

Volumn 62, Issue 14, 1997, Pages 4804-4810

  Dorrestijn, Edwin ^a   Pugin, Raphaël ^a   Nogales, M Victoria Ciriano ^a   Mulder, Peter ^a  

^a LEIDEN UNIVERSITY   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000475967     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9701694     Document Type: Article

References (66)

1. Arends, I. W. C. E.; Louw, R.; Mulder, P. J. Phys. Chem. 1993, 97, 7914-7925.
2. Scheppingen, W.; Dorrestijn, E.; Arends, I.; Mulder, P.; Korth, H. G. J. Phys. Chem., in press.
3. Schraa, G. J.; Arends, I. W. C. E.; Mulder, P. J. Chem. Soc., Perkin Trans. 2 1994, 189-197.
4. Boels, E.; Epema, O.; Mulder, P. To be published.
5. Dorrestijn, E.; Santos Gonzalez, C.; Mulder, P. To be published.
6. Shevchenko, S. M.; Apushkinskii, A. G. Russ. Chem. Rev. 1992, 61, 105-131.
7. (a) Paul, G. C.; Gajewski, J. J. J. Org. Chem. 1993, 58, 5060-
8. (b) Diao, L.; Yang, C.; Wan, P. J. Am. Chem. Soc. 1995, 117, 5369-5370.
9. (c) Katada, T.; Eguchi, S.; Esaki, T.; Sasaki, T. J. Chem. Soc., Perkin Trans. 1 1984, 2649-2653.
10. (d) Yato, M.; Ohwada, T.; Shudo, K. J. Am. Chem. Soc. 1990, 112, 5341-5342.
11. (e) Chapman, O. L.; McIntosh, C. L. J. Chem. Soc., Chem. Commun. 1971, 383-384.
12. (a) Wentrup, C.; Müller, P. Tetrahedron Lett. 1973, 2915-2918.
13. (b) Wentrup, C. Tetrahedron Lett. 1973, 2919-2922.
14. Turner, A. B. Q. Rev. Chem. Soc. 1964, 18, 347-360.
15. (a) Gardner, P. D.; Sarrafizadeh R. H.; Brandon, R. L. J. Am. Chem. Soc. 1959, 81, 5515.
16. (b) Cavitt, S. B.; Sarrafizadeh R., H.; Gardner, P. D. J. Org. Chem. 1962, 27, 1211-1216.
17. (a) Eck, V.; Schweig, A.; Vermeer, H. Tetrahedron Lett. 1978, 27, 2433-2436.
18. (b) McIntosh, C. L.; Chapman, O. L. J. Chem. Soc., Chem. Commun. 1996, 771.
19. (c) Mao, Y. L.; Boekelheide, V. Proc. Nat. Acad. Sci. U.S.A. 1980, 77, 1732-1735.
20. Inoue, T.; Inoue, S.; Sato, K. Chem. Lett. 1989, 653-656.
21. Chapman, O. L.; McIntosh, C. L.; Clardy, J. C. J. Chem. Soc., Chem. Commun. 1971, 384-385.
22. 2 in propene. This also leads to 2-methylchroman.
23. Fleming, I. Frontier Orbitals and Organic Chemical Reactions; John Wiley: London, 1976.
24. Fulvene was generated in a separate experiment by recombination of cyclopentadienyl radicals with chloromethyl radicals and subsequent elimination of HCl.
25. Mallard, W. G.; Westley, F.; Herron, J. T.; Hampson, R. F. NIST Chemical Kinetics Database, version 5.0; NIST Standard Reference Data, National Institute of Standards and Technology: Gaithersburg, MD, 1993.
26. Moore, J. W.; Pearson, R. G. Kinetics and Mechanism, 3rd ed.; John Wiley: New York, 1981; p 291.
27. Tsang, W.;Cui, J. P. J. Am. Chem. Soc. 1990, 112, 1665-1671.
28. Houk, K. N.; Gonzalez, J.; Li, Y. Acc. Chem. Res. 1995, 281 81-90.
29. -1. Since both approaches resulted in the same value it can be concluded that an additional ring strain component is negligible, in accordance with ref 28.
30. Colussi, A. J.; Zabel, F.; Benson, S. W. Int. J. C. Chem. Kinet. 1977, 9, 161-178.
31. Suryan, M. M.; Kafafi, S. A.; Stein, S. E. J. Am. Chem. Soc. 1989, 111, 4594-4600.
32. Stein, S. E.; Rukkers, J. M.; Brown, R. L. NIST Structures and Properties Database, version 2.0; NIST Standard Reference Data, National Institute of Standards and Technology: Gaithersburg, MD, 1994.
33. Wayner, D. D. M.; Lusztyk, E.; Ingold, K. U.; Mulder, P. J. Org. Chem. 1996, 61, 6430-6433.
34. Jonsson, M.; Lind, J.; Eriksen, T. E.; Merényi, G. J. Chem. Soc., Perkin Trans. 2 1993, 1567-1568.
35. Hansch, C.; Leo, A.; Taft, R. W. Chem. Rev. 1991, 91, 165- 195.
36. Cohen, N. J. Phys. Chem. Ref. Data. 1996, 25, 1411-1481.
37. Tsang, W. Int. J. Chem. Kinet. 1973, 5, 651-662.
38. This work.
39. Taylor, R. J. Chem. Soc., Perkin Trans. 2 1988, 183-189.
40. Chirico, R. D.; Archer, D. G.; Hossenlopp, I. A.; Nguyen, A.; Steele, W. V.; Gammon, B. E. J. Chem. Thermodyn. 1990, 22, 665- 682.
41. Dorofeeva, O. V. Thermochim. Acta 1992, 200, 121-150.
42. 2 in 1,3-cyclohexadiene to give 5-methylene-1,3-
43. -1.
44. Sauer, J.; Sustmann, R. Angew. Chem. 1980, 92, 773-801.
45. (a) Charlton, J. L.; Alauddin, M. M. Tetrahedron 1987, 43, 2873-2889.
46. (b) Sato, H.; Isono, N.; Okamura, K.; Date, T.; Mori, M. Tetrahedron Lett. 1994, 35, 2035-2038.
47. (c) Fleming, I.; Gianni, F. L.; Man, T. Tetrahedron Lett. 1976, 881-884.
48. Gajewski, J. J.; Paul, G. C. J. Org. Chem. 1990, 55, 4575-4581.
49. Horn, B. A.; Herek, J. L.; Zewail, A. H. J. Am. Chem. Soc. 1996, 118, 8755-8756.
50. Letulle, M.; Guenot, P.; Ripoll, J. L. Tetrahedron Lett. 1991, 32, 2013-2016.
51. -1 (addition to C=O).
52. Berkowitz, J.; Ellison, G. B.; Gutman, D. J. Phys. Chem. 1994, 98, 2744-2765.
53. -1.
54. Savage, P. E. Energy Fuels 1995, 9, 590-598.
55. -7 M.
56. -1.
57. (a) Ciriano Nogales, M. V.; Dorrestijn, E.; Mulder, P. To be published. For experimental details:
58. (b) Arends, I. W. C. E.; Mulder, P. Energy Fuels 1996, 10, 235-242.
59. Gaynor, B. J.; Gilbert, R. G.; King, K. D.; Harman, P. J. Aust. J. Chem. 1981, 34, 449-452.
60. (a) Buxton, J. P.; Simpson, C. J. S. M. Chem. Phys. 1986, 105, 307-316,
61. (b) Dolbier, W. R.; Frey, H. M. J. Chem. Soc., Perkin Trans. 2 1974, 1674-1676.
62. Frey, H. M.; Hopf, H. J. Chem. Soc., Perkin Trans. 2 1973, 2016-2019.
63. -1.
64. Dorrestijn, E.; Mulder, P. J. Anal. Appl. Pyrolysis, submitted.
65. Deady, I. W.; Topsom, R. D.; Vaughan, J. J. Chem. Soc. 1963, 2094-2095.
66. Trudell, J. R.; Sample Woodgate, D.; Djerassi, C. Org. Mass Spectrom. 1970, 3, 753-776.