From phenylenes to acenes: Flash vacuum pyrolytic isomerization of angular [3]phenylene to benzo[ghi]fluoranthene

Chemical Communications

Volumn , Issue 15, 1997, Pages 1415-1416

  Matzger, Adam J ^a   Vollhardt, K Peter C ^a  

^a NONE

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0010233146     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a702680c     Document Type: Article

References (20)

1. (a) L. T. Scott, Pure Appl. Chem., 1996, 68, 291;
2. (b) P. W. Rabideau and A. Sygula, Acc. Chem. Res., 1996, 29, 235;
3. (c) R. F. C. Brown and F. W. Eastwood, Pure Appl. Chem., 1996, 68, 261;
4. (d) L. W. Jenneskens, M. Sarobe and J. W. Zwikker, Pure Appl. Chem., 1996, 68, 219.
5. U. E. Wiersum, Janssen Chim. Acta, 1992, 10, 3.
6. R. Diercks and K. P. C. Vollhardt, Angew. Chem., 1986, 98, 268; Angew. Chem., Int. Ed. Engl., 1986, 25, 266.
7. R. Diercks and K. P. C. Vollhardt, Angew. Chem., 1986, 98, 268; Angew. Chem., Int. Ed. Engl., 1986, 25, 266.
8. B. C. Berris, G. H. Hovakeemian, Y.-H. Lai, H. Mestdagh and K. P. C. Vollhardt, J. Am. Chem. Soc., 1985, 107, 5670.
9. R. Diercks and K. P. C. Vollhardt, J. Am. Chem. Soc., 1986, 108, 3150
10. J. W. Barton and R. B. Walker, Tetrahedron Lett., 1978, 1005.
11. W. Karcher, R. J. Fordham, J. J. Dubois, P. G. J. M. Glaude and J. A. M. Ligthart, Spectral Atlas of Polycyclic Aromatic Compounds, Reidel, Dordrecht, 1985.
12. The synthesis of acepentalene and its tribenzo derivative have recently been reported: R. Haag, D. Schröder, T. Zywietz, H. Jiao, H. Schwarz, P. von R. Schleyer and A. de Meijere, Angew. Chem., 1996, 108, 1413; Angew. Chem., Int. Ed. Engl., 1996, 35, 1317; R. Haag, B. Ohlhorst, M. Noltemeyer, R. Fleischer, D. Stalke, A. Schuster, D. Kuck and A. de Meijere, J. Am. Chem. Soc., 1995, 117, 10474.
13. The synthesis of acepentalene and its tribenzo derivative have recently been reported: R. Haag, D. Schröder, T. Zywietz, H. Jiao, H. Schwarz, P. von R. Schleyer and A. de Meijere, Angew. Chem., 1996, 108, 1413; Angew. Chem., Int. Ed. Engl., 1996, 35, 1317; R. Haag, B. Ohlhorst, M. Noltemeyer, R. Fleischer, D. Stalke, A. Schuster, D. Kuck and A. de Meijere, J. Am. Chem. Soc., 1995, 117, 10474.
14. The synthesis of acepentalene and its tribenzo derivative have recently been reported: R. Haag, D. Schröder, T. Zywietz, H. Jiao, H. Schwarz, P. von R. Schleyer and A. de Meijere, Angew. Chem., 1996, 108, 1413; Angew. Chem., Int. Ed. Engl., 1996, 35, 1317; R. Haag, B. Ohlhorst, M. Noltemeyer, R. Fleischer, D. Stalke, A. Schuster, D. Kuck and A. de Meijere, J. Am. Chem. Soc., 1995, 117, 10474.
15. G. Zimmermann, U. Nuechter, S. Hagen and M. Nuechter, Tetrahedron Lett., 1994, 35, 4747; R. F. C. Brown, N. Choi, K. J. Coulston, F. W. Eastwood, U. E. Wiersum and L. J. Jenneskens, Tetrahedron Lett., 1994, 35, 4405.
16. G. Zimmermann, U. Nuechter, S. Hagen and M. Nuechter, Tetrahedron Lett., 1994, 35, 4747; R. F. C. Brown, N. Choi, K. J. Coulston, F. W. Eastwood, U. E. Wiersum and L. J. Jenneskens, Tetrahedron Lett., 1994, 35, 4405.
17. U. E. Wiersum and L. W. Jenneskens, Tetrahedron Lett., 1993, 34, 6615.
18. K. N. Bharucha, R. M. Marsh, R. E. Minto and R. G. Bergman, J. Am. Chem. Soc., 1992, 114, 3120.
19. G. M. Badger, J. Chem. Soc., 1941, 535.
20. The rapid hydrogenation of dibenzofulvene by a radical mechanism has been observed: T. E. Nalesnik, J. H. Freudenberger and M. Orchin, J. Organomet. Chem., 1981, 221, 193.