Isomerization of linear to angular [3]phenylene and PAHs under flash vacuum pyrolysis conditions

Organic Letters

Volumn 3, Issue 7, 2001, Pages 1017-1020

  Dosa, Peter I ^a   Schleifenbaum, Andreas ^a   Vollhardt, K Peter C ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

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EID: 0000933533     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.5555/ol015519u     Document Type: Article

References (25)

1. (a) Matzger, A. J.; Vollhardt, K. P. C. Chem. Commun. 1997, 1415.
2. (b) Wiersum, U. E.; Jenneskens, L. W. Tetrahedron Lett. 1993, 34, 6615.
3. (c) Brown, R. F. C.; Choi, N.; Coulston, K. J.; Eastwood, F. W.; Wiersum, U. E.; Jenneskens, L. W. Tetrahedron Lett. 1994, 35, 4405.
4. (a) Preda, D. V.; Scott, L. T. Org. Lett. 2000, 2, 1489.
5. (b) See also: Sarobe, M.; Kwint, H. C.; Fleer, T.; Havenith, R. W. A.; Jenneskens, L. W.; Vlietstra, E. J.; van Lenthe, J. H.; Wesseling, J. Eur. J. Org. Chem. 1999, 1191.
6. Berris, B. C.; Hovakeemian, G. H.; Lai, Y.; Mestdagh, H.; Vollhardt, K. P. C. J. Am. Chem. Soc. 1985, 107, 5670.
7. The products were separated by HPLC and their identities confirmed by comparison of their NMR and UV spectra with those published in the literature. For spectra of 3 and 6. see: Sarobe, M.; Jenneskens, L. W. J. Org. Chem. 1997, 62, 8247. Karcher, W.; Fordham, R. J.; Dubois, J. J.; Glaude, P. G. J. M.; Ligthart, J. A. M. Spectral Atlas of Polycyclic Aromatic Compounds, Reidel: Dordrecht, 1985. For spectra of 4, see: Sarobe, M.; Snoeijer, J. D.; Jenneskens, L. W.; Slagt, M. Q.; Zwikker, J. W. Tetrahedron Lett. 1995, 36, 8489. For spectra of 5, see: Mulder, P. P. J.; Boere, B. B.; Cornelisse, J.; Lugtenburg, J. Recl. Trav. Chim. Pay-Bas 1993, 112, 255.
8. The products were separated by HPLC and their identities confirmed by comparison of their NMR and UV spectra with those published in the literature. For spectra of 3 and 6. see: Sarobe, M.; Jenneskens, L. W. J. Org. Chem. 1997, 62, 8247. Karcher, W.; Fordham, R. J.; Dubois, J. J.; Glaude, P. G. J. M.; Ligthart, J. A. M. Spectral Atlas of Polycyclic Aromatic Compounds, Reidel: Dordrecht, 1985. For spectra of 4, see: Sarobe, M.; Snoeijer, J. D.; Jenneskens, L. W.; Slagt, M. Q.; Zwikker, J. W. Tetrahedron Lett. 1995, 36, 8489. For spectra of 5, see: Mulder, P. P. J.; Boere, B. B.; Cornelisse, J.; Lugtenburg, J. Recl. Trav. Chim. Pay-Bas 1993, 112, 255.
9. The products were separated by HPLC and their identities confirmed by comparison of their NMR and UV spectra with those published in the literature. For spectra of 3 and 6. see: Sarobe, M.; Jenneskens, L. W. J. Org. Chem. 1997, 62, 8247. Karcher, W.; Fordham, R. J.; Dubois, J. J.; Glaude, P. G. J. M.; Ligthart, J. A. M. Spectral Atlas of Polycyclic Aromatic Compounds, Reidel: Dordrecht, 1985. For spectra of 4, see: Sarobe, M.; Snoeijer, J. D.; Jenneskens, L. W.; Slagt, M. Q.; Zwikker, J. W. Tetrahedron Lett. 1995, 36, 8489. For spectra of 5, see: Mulder, P. P. J.; Boere, B. B.; Cornelisse, J.; Lugtenburg, J. Recl. Trav. Chim. Pay-Bas 1993, 112, 255.
10. The products were separated by HPLC and their identities confirmed by comparison of their NMR and UV spectra with those published in the literature. For spectra of 3 and 6. see: Sarobe, M.; Jenneskens, L. W. J. Org. Chem. 1997, 62, 8247. Karcher, W.; Fordham, R. J.; Dubois, J. J.; Glaude, P. G. J. M.; Ligthart, J. A. M. Spectral Atlas of Polycyclic Aromatic Compounds, Reidel: Dordrecht, 1985. For spectra of 4, see: Sarobe, M.; Snoeijer, J. D.; Jenneskens, L. W.; Slagt, M. Q.; Zwikker, J. W. Tetrahedron Lett. 1995, 36, 8489. For spectra of 5, see: Mulder, P. P. J.; Boere, B. B.; Cornelisse, J.; Lugtenburg, J. Recl. Trav. Chim. Pay-Bas 1993, 112, 255.
11. Jacob, J. Pure Appl. Chem. 1996, 68, 301.
12. Schulman, J. M.; Disch, R. L. J. Am. Chem. Soc. 1996, 118, 8470.
13. 3 and 6 are known to interconvert at temperatures greater than those used in the present study, see: Plater, M. J. Tetrahedron Lett. 1994, 35, 6147. Jenneskens, L. W.; Sarobe, M.; Zwikker, J. W. Pure Appl. Chem. 1996, 68, 219.
14. 3 and 6 are known to interconvert at temperatures greater than those used in the present study, see: Plater, M. J. Tetrahedron Lett. 1994, 35, 6147. Jenneskens, L. W.; Sarobe, M.; Zwikker, J. W. Pure Appl. Chem. 1996, 68, 219.
15. Negishi, E.; Kotora, M.; Xu, C. J. Org. Chem. 1997, 62, 8957.
16. Diercks, R.; Eaton, B. E.; Gürtzgen, S.; Jalisatgi, S.; Matzger, A. J.; Radde, R. H.; Vollhardt, K. P. C. J. Am. Chem. Soc. 1998, 120, 8247.
17. 13C NMR spectrum.
18. For recent mechanistic reviews, see: (a) Necula, A.; Scott, L. T. J. Anal. Appl. Pyrol. 2000, 54, 65.
19. (b) Brown, R. F. C. Eur. J. Org. Chem. 1999, 3211.
20. See: Slanina, Z.; Zhao, X.; Uhlík, F.; Ozawa, M.; Osawa, E. J. Organomet. Chem. 2000, 599, 57, and references therein.
21. Beckhaus, H.-D.; Faust, R.; Matzger, A. J.; Mohler, D. L.; Rogers, D. W.; Rüchardt, C.; Sawhney, A. K.; Verevkin, S. P.; Vollhardt, K. P. C.; Wolff, S. J. Am. Chem. Soc. 2000, 122, 7819.
22. The synthesis of acepentalene and its tribenzo derivative have been reported: Haag, R.; Schröder, D.; Zywietz, T.; Jiao, H.; Schwarz, H.; Schleyer, P. v. R.; de Meijere, A.; Angew. Chem., Int. Ed. Engl. 1996, 35, 1317. Haag, R.; Ohlhorst, B.; Noltemeyer, M.; Fleischer, R.; Stalke, D.; Schuster, A.; Kuck, D.; de Meijere, A. J. Am. Chem. Soc. 1995, 117, 10474.
23. The synthesis of acepentalene and its tribenzo derivative have been reported: Haag, R.; Schröder, D.; Zywietz, T.; Jiao, H.; Schwarz, H.; Schleyer, P. v. R.; de Meijere, A.; Angew. Chem., Int. Ed. Engl. 1996, 35, 1317. Haag, R.; Ohlhorst, B.; Noltemeyer, M.; Fleischer, R.; Stalke, D.; Schuster, A.; Kuck, D.; de Meijere, A. J. Am. Chem. Soc. 1995, 117, 10474.
24. Vollhardt, K. P. C.; Mohler, D. L. In Advances in Strain in Organic Chemistry; Halton, B., Ed.; JAI: London, 1996; pp 121-160.
25. For a review, see: Wiersum, U. E.; Jenneskens, L. W. In Gas-Phase Reactions in Organic Symthesis; Vallée, Y., Ed.; Gordon and Breach: Amsterdam, 1997; pp 143-194.