Origin of pyrene under high temperature conditions in the gas phase. The pivotal role of phenanthrene

Journal of Organic Chemistry

Volumn 64, Issue 11, 1999, Pages 3861-3866

  Sarobe, Martin ^a   Jenneskens, Leonardus W ^a   Steggink, Ralph G B ^a   Visser, Tom ^b  

^a UTRECHT UNIVERSITY   (Netherlands)

^b NATIONAL INSTITUTE FOR PUBLIC HEALTH AND THE ENVIRONMENT   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

PHENANTHRENE; PYRENE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL INTERACTION; CHEMICAL REACTION; CHEMICAL STRUCTURE; HIGH TEMPERATURE; MOLECULAR DYNAMICS; PHYSICAL CHEMISTRY; SYNTHESIS;

EID: 0033612290     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo982030e     Document Type: Article

References (38)

1. Lafleur, A. L.; Longwell, J. P.; Shirnamé-Moré, L.; Monchamp, P. A.; Peters, W. A.; Plummer, E. F. Energy Fuels, 1990, 4, 307 and references cited. Howard, J. B.; Longwell, J. P.; Marr, J. A.; Pope, C. J.; Busby, W. F., Jr.; Lafleur, A. L.; Taghizadeh, K. Combust. Flame 1995, 101, 262 and references cited.
2. Lafleur, A. L.; Longwell, J. P.; Shirnamé-Moré, L.; Monchamp, P. A.; Peters, W. A.; Plummer, E. F. Energy Fuels, 1990, 4, 307 and references cited. Howard, J. B.; Longwell, J. P.; Marr, J. A.; Pope, C. J.; Busby, W. F., Jr.; Lafleur, A. L.; Taghizadeh, K. Combust. Flame 1995, 101, 262 and references cited.
3. Harvey, R. G. In Polycyclic Aromatic Hydrocarbons: Chemistry and Carcinogenicity; Cambridge University Press: Cambridge, England, 1991. Harvey, R. G. In Polycyclic Aromatic Hydrocarbons; Wiley- VCH: New York, 1997.
4. Harvey, R. G. In Polycyclic Aromatic Hydrocarbons: Chemistry and Carcinogenicity; Cambridge University Press: Cambridge, England, 1991. Harvey, R. G. In Polycyclic Aromatic Hydrocarbons; Wiley-VCH: New York, 1997.
5. Senthilnathan, V. P.; Stein, S. E. J. Org. Chem. 1988, 53, 1988. Wornat, M. J.; Lafleur, A. L.; Sarofim, A. F. Polycyclic Aromat. Compd. 1993, 3, 149 and references cited.
6. Senthilnathan, V. P.; Stein, S. E. J. Org. Chem. 1988, 53, 1988. Wornat, M. J.; Lafleur, A. L.; Sarofim, A. F. Polycyclic Aromat. Compd. 1993, 3, 149 and references cited.
7. Bockhorn, H.; Fetting, F.; Wenz, H. W. Ber. Bunsen-Ges. Phys. Chem., 1983, 87, 1067. Lafleur, A. L.; Gagel, J. J.; Longwell, J. P.; P. A. Monchamp, P. A. Energy Fuels 1988, 2, 709 and references cited. Baum, T.; Löffler, S.; Löffler, P.; Weilmünster, P.; Homann, K.-H. Ber. Bunsen-Ges. Phys. Chem. 1992, 96, 841.
8. Bockhorn, H.; Fetting, F.; Wenz, H. W. Ber. Bunsen-Ges. Phys. Chem., 1983, 87, 1067. Lafleur, A. L.; Gagel, J. J.; Longwell, J. P.; P. A. Monchamp, P. A. Energy Fuels 1988, 2, 709 and references cited. Baum, T.; Löffler, S.; Löffler, P.; Weilmünster, P.; Homann, K.-H. Ber. Bunsen-Ges. Phys. Chem. 1992, 96, 841.
9. Bockhorn, H.; Fetting, F.; Wenz, H. W. Ber. Bunsen-Ges. Phys. Chem., 1983, 87, 1067. Lafleur, A. L.; Gagel, J. J.; Longwell, J. P.; P. A. Monchamp, P. A. Energy Fuels 1988, 2, 709 and references cited. Baum, T.; Löffler, S.; Löffler, P.; Weilmünster, P.; Homann, K.-H. Ber. Bunsen-Ges. Phys. Chem. 1992, 96, 841.
10. For recent reviews: Eastwood, F. W. In Gas-Phase Reactions in Organic Synthesis; Vallée, Y., Ed.; Gordon and Breach Science Publishers: New York, 1997; Chapter 1 and references cited. Wiersum, U. E.; Jenneskens, L. W. In Gas-Phase Reactions in Organic Synthesis, Vallée, Y., Ed.; Gordon and Breach Science Publishers: New York, 1997; Chapter 3 and references cited.
11. For recent reviews: Eastwood, F. W. In Gas-Phase Reactions in Organic Synthesis; Vallée, Y., Ed.; Gordon and Breach Science Publishers: New York, 1997; Chapter 1 and references cited. Wiersum, U. E.; Jenneskens, L. W. In Gas-Phase Reactions in Organic Synthesis, Vallée, Y., Ed.; Gordon and Breach Science Publishers: New York, 1997; Chapter 3 and references cited.
12. For example: Tan, Y.L.; Kong, A.; Monetti, M. A. Polycyclic Aromat. Compd. 1996, 9, 185 and references cited.
13. Brown, R. F. C. Pyrolytic Methods in Organic Chemistry; Academic Press: New York, 1980; Chapters 1 and 2.
14. For reviews: Jenneskens, L. W.; Sarobe, M.; Zwikker, J. W. Pure Appl. Chem. 1996, 68, 219 and references cited. Scott, L. T. Pure Appl. Chem. 1996, 68, 291 and references cited.
15. For reviews: Jenneskens, L. W.; Sarobe, M.; Zwikker, J. W. Pure Appl. Chem. 1996, 68, 219 and references cited. Scott, L. T. Pure Appl. Chem. 1996, 68, 291 and references cited.
16. Brown, R. F. C.; Eastwood, F. W.; Harrington, K. J.; McMullen, G. L. Austr. J. Chem. 1974, 27, 2393.
17. For an example: Sarobe, M.; Flink, S.; Jenneskens, L. W.; van Poecke, B. L. A.; Zwikker, J. W. J. Chem. Soc., Chem. Commun. 1995, 2415. Scott, L. T.; Necula, A. J. Org. Chem. 1996, 61, 386.
18. For an example: Sarobe, M.; Flink, S.; Jenneskens, L. W.; van Poecke, B. L. A.; Zwikker, J. W. J. Chem. Soc., Chem. Commun. 1995, 2415. Scott, L. T.; Necula, A. J. Org. Chem. 1996, 61, 386.
19. 12
20. Sarobe, M.; Jenneskens, L. W.; Wesseling, J.; Snoeijer, J. D.; Zwikker, J. W.; Wiersum, U. E. Liebigs Ann./Recueil 1997, 1207 and references cited.
21. Sarobe, M.; Jenneskens, L. W.; Wesseling, J.; Wiersum, U. E. J. Chem. Soc., Perkin 2 1997, 703 and references cited.
22. For a recent example: Hofmann, J.; Zimmermann, G.; Guthier, K.; Hebgen, P.; Homann, K.-H. Liebigs Ann. 1995, 631 and references cited.
23. Sarobe, M.; van Heerbeek, R.; Jenneskens, L. W.; Zwikker, J. W. Liebigs Ann./Recueil 1997, 2499 and references cited.
24. Sarobe, M.; Jenneskens, L. W.; Kleij, A.; Petroutsa, M. Tetrahedron Lett. 1997, 38, 7255.
25. See also: Hofmann, J.; Zimmerman, G.; Findeisen, M. Tetrahedron Lett., 1995, 36, 3831. Scott, L. T.; Necula, A. Tetrahedron Lett. 1997, 38, 1877.
26. See also: Hofmann, J.; Zimmerman, G.; Findeisen, M. Tetrahedron Lett., 1995, 36, 3831. Scott, L. T.; Necula, A. Tetrahedron Lett. 1997, 38, 1877.
27. Sarobe, M.; Flink, S.; Jenneskens, L. W.; Zwikker, J. W.; Wesseling, J. J. Chem. Soc., Perkin Trans. 2 1996, 2125 and references cited.
28. See also: Brown, R. F. C.; Eastwood, F. W.; Wong, N. R. Tetrahedron Lett. 1993, 34, 1223 and references cited.
29. Dewar, M. J. S.; Zoebisch, E. G.; Healy, E. F.; Stewart, J. J. P. J. Am. Chem. Soc. 1985, 107, 3902.
30. Mallory, F. B.; Baker, M. B. J. Org. Chem. 1984, 49, 1323.
31. Gore, P. H. In Friedel Crafts and Related Reactions, Olah, G. A., Ed.; Interscience: New York, 1964; Vol. III, pp 78-80.
32. Visser, T.; Sarobe, M.; Jenneskens, L. W.; Wesseling, J. Fuel 1998, 77, 913.
33. Brown, R. F. C.; Coulston; K. J.; Eastwood, F. W. Tetrahedron Lett. 1996, 37, 6819. The occurrence of fragmentation reactions is supported by the observation of carbonization in the hot zone concomitant with a decrease in mass recovery.
34. Lafleur, A. L.; Howard, J. B.; Taghizadeh, K.; Plummer, E. F.; Scott. L. T.; Necula, A.; Swallow, K. C. J. Phys. Chem. 1996, 100, 17421 and references cited.
35. -1] is attributed to steric strain between the ethynyl substituent and the phenanthrene hydrogen atom at the 5-position, respectively (see also ref 21).
36. Cyclobuta-PAH formation is expected to occur in the dilute gas phase. Cf. the stability of benzocyclobutadiene, which dimerizes above -190°C; Chapmann, O. L.; Chang, C. C.; Rosenquist, N. R., J. Am. Chem. Soc. 1976, 98, 261. For recent ab initio calculations on benzocyclobutadiene: Schulman, J. M.; Disch, R. L. J. Am. Chem. Soc., 1993, 115, 11153 and references cited.
37. Cyclobuta-PAH formation is expected to occur in the dilute gas phase. Cf. the stability of benzocyclobutadiene, which dimerizes above -190°C; Chapmann, O. L.; Chang, C. C.; Rosenquist, N. R., J. Am. Chem. Soc. 1976, 98, 261. For recent ab initio calculations on benzocyclobutadiene: Schulman, J. M.; Disch, R. L. J. Am. Chem. Soc., 1993, 115, 11153 and references cited.
38. Hopkins, N. E.; Forooezsh, M. K.; Alworth, W. L. Biochem. Pharmacol. 1992, 44, 787.