Phenyl migrations in dehydroaromatic compounds. A new mechanistic link between alternant and nonalternant hydrocarbons at high temperatures

Organic Letters

Volumn 2, Issue 10, 2000, Pages 1489-1492

  Preda, Dorin V ^a   Scott, Lawrence T ^a  

^a BOSTON COLLEGE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0011801341     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol005849z     Document Type: Article

References (36)

1. (a) Preda, D. V.; Scott, L. T. Polycyclic Aromat. Compd., in press.
2. (b) Scott, L. T.; Preda, D. V. Abstracts of Papers, 218th National Meeting of the American Chemical Society, New Orleans, LA, Aug. 1999; American Chemical Society: Washington, D C, 1999; ORGN-500.
3. (c) Preda, D. V.; Scott, L. T. Seventeenth International Symposium on Polycyclic Aromatic Compounds, Bordeaux, France, Oct, 1999, abstract 138.
4. (a) Jensen, F. R.; Coleman, W. E. Tetrahedron Lett. 1959, No. 20, 7-11.
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6. 4 At 900 °C, the mass recovery was 75% (75 mg), whereas at 1100 °C, the mass recovery was 70% (70 mg). Approximately 30-35% of unchanged 1 was recovered from the 900 °C pyrolysis, but none survives in the 1100 °C pyrolysis.
7. Scott, L. T.; Bratcher, M. S.; Hagen, S. J. Am. Chem. Soc. 1996, 118, 8743-4.
8. 6 The numbers reported for fluoranthene (3) at 1100 °C therefore represent the sum of the concentrations of fluoranthene and acephenanthrylene.
9. (a) Scott, L. T.; Roelofs, N. H. J. Am. Chem. Soc. 1987, 109, 5461
10. (b) Scott, L. T.; Roelofs, N. H. Tetrahedron Lett. 1988, 29, 6857-60.
11. (c) Anderson, M. R.; Brown, R. F. C.; Coulston, K. J.; Eastwood, F. W.; Ward, A. Aust. J. Chem. 1990, 43, 1137-50.
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13. (a) Wiersum, U. E.; Jenneskens, L. W. Tetrahedron Lett. 1993, 34, 6615-18.
14. (b) Brown, R. F. C.; Choi, N.; Coulston, K. J.; Eastwood, F. W.; Wiersum, U. E.; Jenneskens, L. W. Tetrahedron Lett. 1994, 35, 4405-8.
15. Scott, L. T.; Hashemi, M. M.; Schultz, T. H.; Wallace, M. B. J. Am. Chem. Soc. 1991, 113, 9692-3.
16. 2 carbon-carbon single bonds, see: (a) Sarobe, M.; Kwint, H. C.; Fleer, T.; Jenneskens, L. W.; Wesseling, J. Tetrahedron Lett. 1998, 39, 9823-6.
17. (b) Sarobe, M.; Kwint, H. C.; Fleer, T.; Hevenith, R. W. A.; Jenneskens, L. W.; Vlietstra, E. J.; Van Lenthe, J. H.; Wesseling, J. Eur. J. Org. Chem. 1999, 1191-1200.
18. Brown, R. F. C.; Choi, N.; Eastwood, F. W. Aust. J. Chem. 1995, 48, 185-98.
19. Bratcher, M. S. Ph.D. Dissertation, Boston College, Chestnut Hill, MA, 1996.
20. Cioslowski, J.; Liu, G.; Moncrieff, D. J. Org. Chem. 1996, 61, 4111-4.
21. Latif, A.; Soliman, G. J. Chem. Soc. 1944, 56-8.
22. 5
23. Purchased from Aldrich Chemical Co.
24. 5
25. See, for example: (a) Howard, J. B.; Lafleur, A. L.; Makarovsky, Y.; Mitra, S.; Pope, C. J.; Yadav, T. K. Carbon 1992, 30, 1183-201.
26. (b) Ahrens, J.; Bachmann, M.; Baum, T.; Griesheimer, J.; Kovacs, R.; Weilmuenster, P.; Homann, K. H. Int. J. Mass Spectrom. Ion Processes 1994, 138, 133-48.
27. (c) Homann, K.-H. Angew. Chem., Int. Ed. Engl. 1998, 37, 2435-51.
28. (d) Richter, H.; Grieco, W. J.; Howard, J. B. Chem. Phys. Processes Combust. 1997, 135-138.
29. (e) Richter, H.; Grieco, W. J.; Howard, J. B. Combust. Flame 1999, 119, 1-22.
30. (f) Marr, L. C.; Kirchstetter, T. W.; Harley, R. A.; Miguel, A. H.; Hering, S. V.; Hammond, S. K. Environ. Sci. Technol. 1999, 33, 3091-9.
31. (a) Scott, L. T. Pure Appl. Chem. 1996, 68, 291-300.
32. (b) Neilen, R. H. G.; Wiersum, U. E. Chem. Commun. 1996, 149-50.
33. (c) Sarobe, M.; Jenneskens, L. W.; Wiersum, U. E. Tetrahedron Lett. 1996, 37, 1121-2.
34. (d) Matzger, A. J.; Vollhardt, K. P. C. Chem. Commun. 1997, 1415-6.
35. (e) Necula, A.; Scott, L. T. J. Anal. Appl. Pyrolysis 2000, 54, 65-87.
36. For acid-catalyzed phenyl group migrations around the perimeter of aromatic hydrocarbons, see: Necula, A.; Racoveanu-Schiketanz, A.; Gheorghiu, M. D.; Scott, L. T. J. Org. Chem. 1995, 60, 3448-51 and references therein.