Flash vacuum thermolysis of 5-(1-chloroethenyl)acenaphthene. A short synthesis of pyracylene and its behaviour under high temperature conditions

Journal of the Chemical Society. Perkin Transactions 2

Volumn 10, Issue , 1996, Pages 2125-2131

  Sarobe, Martin ^a   Flink, Simon ^a   Jenneskens, Leonardus W ^a   Zwikker, Jan W ^a   Wesseling, Jolanda ^a  

^a UTRECHT UNIVERSITY   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002043353     PISSN: 03009580     EISSN: None     Source Type: Journal    
DOI: 10.1039/p29960002125     Document Type: Article

References (40)

1. B. M. Trost, G. M. Bright, C. Frihart and D. Brittelli, J. Am. Chem. Soc., 1971, 93, 737.
2. B. Freiermuth, S. Gerber, A. Riesen, J. Wirz and M. Zehnder, J. Am. Chem. Soc., 1990, 112, 738 and references cited therein.
3. M. Löffler and A.-D. Schlüter, Synlett, 1994, 75.
4. H. Tani, K. Masumoto, N. Azuma and N. Ono, Chem. Lett., 1994, 779.
5. Cf. R. Taylor and D. R. M. Walton, Nature (London), 1993, 363, 685.
6. S. E. Stein and A. Fahr, J. Phys. Chem., 1985, 89, 3714.
7. G. J. Schaden, J. Org. Chem., 1983, 48, 5385.
8. E. V. Dehmlov and M. Fründ, Z. Naturforsch., Teil B, 1992, 47, 1647.
9. L. T. Scott and H. B. Warren, 7th International Symposium on Novel Aromatic Compounds, 1992, Victoria, Canada, July 19-24, abstract 65.
10. B. D. Crittenden and R. Long, Environ. Sci. Technol., 1973, 7, 742;
11. J. L. Schultz, T. Kessler, R. A. Friedel and A. G. Sharkey, Fuel, 1972, 51, 242;
12. R. E. Laflamme and R. A. Hites, Geochim. Cosmochim. Acta, 1978, 42, 289.
13. A. J. Stone and D. J. Wales, Chem. Phys. Lett., 1986, 128, 501.
14. M. Sarobe, J. W. Zwikker, J. D. Snoeijer, U. E. Wiersum and L. W. Jennes, J. Chem. Soc., Chem. Commun, 1994, 89;
15. see also R. F. C. Brown and F. W. Eastwood, Synlett, 1993, 9 and references cited therein.
16. R. F. C. Brown, F. W. Eastwood and N. R. Wong, Tetrahedron Lett., 1993, 34, 1223 and references cited therein.
17. M. J. S. Dewar, E. G. Zoebisch, E. F. Healy and J. J. P. Stewart, J. Am. Chem. Soc., 1985, 107, 3902;
18. MOPAC 6.0, J. J. P. Stewart, Quant. Chem. Prog. Exchange, QCPE No. 504, Bloomington, IN, 1990.
19. J. M. Schulman and R. L. Disch, J. Mol. Struct. (THEOCHEM), 1992, 259, 173 and references cited therein.
20. M. Sarobe, J. D. Snoeijer, L. W. Jenneskens, M. Q. Slagt and J. W. Zwikker, Tetrahedron Lett., 1995, 36, 8489.
21. M. L. Lee, G. P. Prado, J. B. Howard and R. A. Hites, Biomed. Mass Spectrom., 1977, 4, 182.
22. Acenaphthylene (11): Y. Yamada and S. Toyoda, Bull. Chem. Soc. Jpn., 1973, 46, 3571;
23. Biphenylene: T. C. W. Mak and H. C. Wong, Top. Cur. Chem., 1987, 140, 141 and references cited therein.
24. M. Sarobe, S. Flink, L. W. Jenneskens, B. L. A. van Poecke and J. W. Zwikker, J. Chem. Soc., Chem. Commun., 1995, 2415;
25. see also L. T. Scott and A. Necula, J. Org. Chem., 1996, 61, 386.
26. A. L. Lafleur, J. J. Gagel, J. P. Longwell and P. A. Monchamp, Energy Fuels, 1988, 2, 709 and references cited therein.
27. For automerization of 11 see L. T. Scott and N. H. Roelofs, Tetrahedron Lett., 1988, 29, 6857.
28. For a less effective synthesis of 3, cf. T. E. O'Boyle, L. J. Scott and B. F. Plummer, J. Org. Chem., 1979, 44, 514.
29. O. Rohde and G. Wegner, Makromol. Chem., 1978, 179, 2013.
30. R. Stephan, Chem. Ber., 1957, 90, 296.
31. P. Hodge, B. J. Hunt and I. H. Shakhshier, Polymer, 1985, 26, 1701.
32. S. Takahashi, Y. Kuroyama, K. Sonogashira and N. Hagihara, Synthesis, 1980, 627.
33. E. Baciocchi, R. Ruzziconi and G. V. Sebastiani, J. Org. Chem., 1982, 47, 3237.
34. L. W. Jenneskens, C. A. M. Hoefs and U. E. Wiersum, J. Org. Chem., 1989, 54, 5811.
35. P. W. Fowler and J. Baker, J. Chem. Soc., Perkin Trans. 2, 1992, 1665;
36. R. L. Murry, D. L. Strout and G. E. Scuseria, Inter. J. of Mass Spectrom. Ion Processes, 1994, 138, 113 and references cited therein;
37. J. M. Hawkins, M. Nambu and A. Meyer, J. Am. Chem. Soc., 1994, 116, 7642 and references cited therein.
38. A. Necula and L. T. Scott, 8th International Symposium on Novel Aromatic Compounds, 1995, Braunschweig, Germany, July 30-August 4, poster 114;
39. see also L. T. Scott, Pure Appl. Chem., 1996, 68, 291.
40. L. W. Jenneskens, M. Sarobe and J. W. Zwikker, Pure Appl. Chem., 1996, 68, 219.