Pyrolysis of silica-immobilized benzyl phenyl ether: Competing radical rearrangement pathways under restricted diffusion

Journal of Organic Chemistry

Volumn 63, Issue 26, 1998, Pages 9895-9903

  Buchanan III, A C ^a   Britt, Phillip F ^a   Todd Skeen, J ^a   Struss, John A ^a   Elam, Chanda L ^a  

^a OAK RIDGE NATIONAL LABORATORY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZHYDRYL DERIVATIVE; BENZOPHENONE DERIVATIVE; BENZYL PHENYL ETHER; SILICON DIOXIDE; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; CHEMICAL BINDING; CHEMICAL REACTION KINETICS; DIFFUSION; ORGANIC CHEMISTRY; PYROLYSIS; REACTION ANALYSIS; REACTION TIME; STRUCTURE ANALYSIS;

EID: 0032567450     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9816717     Document Type: Article

References (68)

1. (a) Gavalas, G. R. Coal Pyrolysis; Elsevier: Amsterdam, 1982.
2. (b) Schlosberg, R. H. Chemistry of Coal Conversion; Plenum: New York, 1985.
3. Bridgwater, A. V., Ed. Thermochemical Processing of Biomass; Butterworth: London, 1984.
4. Stock, L. M. Ace. Chem. Res. 1989, 22, 427.
5. Poutsma, M. L. Energy Fuels 1990, 4, 113.
6. Malhotra, R.; McMillen, D. F. Energy Fuels 1993, 7, 227.
7. (a) Eskay, T. P.; Britt, P. F.; Buchanan, A. C., III. Energy Fuels 1996, 10, 1257.
8. (b) Eskay, T. P.; Britt, P. F.; Buchanan, A. C., III. Energy Fuels 1997, 11, 1278.
9. Manion, J. A.; McMillen, D. F.; Malhotra, R. Energy Fuels 1996, 10, 776.
10. (a) Poutsma, M. L.; Dyer, C. W. J. Org. Chem. 1982, 47, 3367.
11. (b) McMillen, D. F.; Chang, S.-J.; Nigenda, S. E.; Malhotra, R. Prepr. Pap.-Am. Chem. Soc., Div. Fuel Chem. 1985, 30, 414.
12. (a) Meyer, D.; Nicole, D.; Delpuech, J. J. Fuel Proc. Technol 1986, 12, 255.
13. (b) Meyer, D.; Oviawe, P.; Nicole, D.; Lauer, J. C.; Clement, J. Fuel 1990, 69, 1309.
14. (a) King, H.-H.; Stock, L. M. Fuel 1984,63,810.
15. (b) King, H.-H.; Stock, L. M. Fuel 1982, 61, 1172.
16. (a) Korobkov, V. Y.; Grigorieva, E. N.; Bykov, V. I.; Senko, O. V.; Kalechitz, I. V. Fuel 1988,67, 657.
17. (b) Korobkov, V. Y.; Grigorieva, E. N.; Bykov, V. I.; Kalechitz, I. V. Fuel 1988, 67, 663.
18. (a) Schlosberg, R. H.; Davis, W. H., Jr.; Ashe, T. R. Fuel 1981, 60, 201.
19. (b) Ozawa, S.; Sasaki, K; Ogina, Y. Fuel 1986, 65, 707.
20. Wu, B. C.; Klein, M. T.; Sandler, S. I. Energy Fuels 1991, 5, 453.
21. Siskin, M.; Brons, G.; Vaughn, S. N.; Katrizky, A. R.; Balasubramamian, M. Energy Fuels 1990, 4, 488.
22. (e) Suzuki, T.; Yamada, H.; Sears, P. L.; Watanabe, Y. Energy Fuels 1989,3, 707.
23. (f) Makabe, M.; Itoh, H.; Ouchi, K. Fuel 1990, 69, 575.
24. Sato, Y.; Yamakawa, T. Ind. Eng. Chem. Fundam. 1985, 24, 12.
25. (a) Yao, T.; Kamiya, Y. Bull. Chem. Soc. Jpn. 1979, 52, 492.
26. (b) Kamiya, Y.; Yao, T.; Oikawa, S. In Coal Liquefaction Fundamentals; Whitehurst, D. D., Ed.; ACS Symposium Series 139; American Chemical Society: Washington, DC, 1980; pp 291-299.
27. (a) Stein, S. E.Am. Chem. Soc. Symp. Ser. 1981, 169, 97.
28. (b) Miller, R. E.; Stein, S. E. Prepr. Pap.-Am. Chem. Soc., Div. Fuel Chem. 1979,24, 271.
29. 15
30. Britt, P. F.; Buchanan, A. C., Ill; Malcolm, E. A. J. Org, Chem. 1995, 60, 6523 and references therein.
31. P tend to be small and within the accuracy of the estimation procedures.
32. (b) Benson, S. W. Thermochemical Kinetics; Wiley: New York, 1976.
33. Stein, S. E. NIST Structure and Properties Database, Version 2.0, 1994.
34. (a) Green, T.; Kovac, J.; Brenner, D.; Larsen, J. W. In Coal Structure; Meyers, R. A., Ed.; Academic Press: New York, 1982; Chapter 6.
35. (b) Berkowitz, N. The Chemistry of Coal; Elsevier: New York, 1985; Chapter 14.
36. Faulon, J.-L.; Hatcher, P. G. Energy Fuels 1994, 8, 402.
37. (a) Solomon, P. R.; Fletcher, T. H.; Pugmire, R. J. Fuel 1993, 72, 587.
38. (b) Serio, M. A.; Hamblen, D. G.; Markham, J. R.; Solomon, P. R. Energy Fuels 1987, 1, 138.
39. Suuberg, E. M. In Chemistry of Coal Conversion; Schlosberg, R. H., Ed.; Plenum Press: New York, 1985; Chapter 4.
40. Gilot, P.; Stanmore, B. R. Energy Fuels 1995, 9, 126.
41. Buchanan, A. C., HI; Britt, P. F. J. Anal. Appl Pyrolysis In press.
42. (a) Buchanan, A. C., Ill; Britt, P. F.; Thomas, K. B.; Biggs, C. A. J. Am. Chem. Soc. 1996, 118, 2182.
43. (b) Buchanan, A. C., III; Dunstan, T. D. J.; Douglas, E. C.; Poutsma, M. L. J. Am. Chem. Soc. 1986, 108, 7703.
44. Buchanan, A. C., Ill; Biggs, C. A. J. Org. Chem. 1989, 54, 517.
45. Britt, P. F.; Buchanan, A. C., III. J. Org. Chem. 1991, 56, 6132.
46. (e) Buchanan, A. C., III; Britt, P. F.; Thomas, K. B. Energy Fuels 1998,12, 649.
47. (f) Britt, P. F.; Buchanan, A. C., III; Malcolm, E. A.; Biggs, C. A. J. Anal. Appl. Pyrolysis 1993, 25, 407.
48. (g) Buchanan, A. C., III; Britt, P. F. Biggs, C. A. Energy Fuels 1990, 4, 415.
49. (a) Klafter, J.; Drake, J. M., Eds. Molecular Dynamics in Restricted Geometries; Wiley: New York, 1989.
50. (b) Ramamurthy, V., Ed. Photochemistry in Organized and Constrained Media; VCH: New York, 1991.
51. Endo, K.; Koike, T.; Sawaki, T.; Hayashida, O.; Masuda, H.; Aoyama, Y. J. Am. Chem. Soc. 1997, 119, 4117.
52. Pitchumani, K.; Warrior, M.; Ramamurthy, V. J. Am. Chem. Soc. 1996, 118, 9428.
53. (e) Turro, N. J.; Buchachenko, A. L.; Tarasov, V. F. Ace. Chem. Res. 1995, 28, 69.
54. (f) Toda, F. Ace. Chem. Res. 1995,28, 480.
55. (g) Lern, G.; Kaprinidis, N. A.; Schuster, D. I.; Ghatlia, N. D.; Turro, N. J. J. Am. Chem. Soc. 1993, 115, 7009.
56. (h) Laszlo, P. Ace. Chem. Res. 1986, 19, 121.
57. Leon, J. W.; Whitten, D. G. J. Am. Chem. Soc. 1995,117, 2226.
58. Liu, C. C.; Maciel, G. E. J. Am. Chem. Soc. 1996, 118, 5103.
59. -1. Suryan, M. M.; Kafafi, S. A.; Stein, S. E. J. Am. Chem. Soc. 1989, 111, 1423.
60. (a) Omura, K Tetrahedron 1995, 51, 6901 and references therein.
61. (b) Omura, K. J. Org. Chem. 1991, 56, 921.
62. 25
63. McMillen, D. F.; Golden, D. M. Anna. Rev. Phys. Chem. 1982, 33, 493.
64. Collins, C. J.; Roark, W. H.; Raaen, V. F.; Benjamin, B. M. J. Am. Chem. Soc. 1979, 101, 1877.
65. 28
66. Alnajjar, M. A.; Franz, J. A. J. Am. Chem. Soc. 1992, 114, 1052.
67. Choi, C.-Y.; Stock, L. M. J. Org. Chem. 1984, 49, 2871.
68. Buchanan, A. C., Ill; Britt, P. F.; Skeen, J. T. Prepr. Pap.-Am. Chem. Soc., Div. Fuel Chem. 1997, 42, 15.