Formation of naphthodithiophene isomers by flash vacuum pyrolysis of 1,6-di(2-thienyl)- and 1,6-di(3-thienyl)-1,5-hexadien-3-ynes

Comptes Rendus Chimie

Volumn 12, Issue 3-4, 2009, Pages 378-384

  Umeda, Rui ^a   Fukuda, Hiroshi ^a   Miki, Koji ^a   Rahman, S M Abdur ^a   Sonoda, Motohiro ^a   Tobe, Yoshito ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

C C bond formation; Cyclization; Flash vacuum pyrolysis; Naphthodithiophenes

Indexed keywords

EID: 60449107685     PISSN: 16310748     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.crci.2008.09.020     Document Type: Article

References (23)

1. For recent reviews, see:
2. Anthony J.E. Chem. Rev. 106 (2006) 5028
3. Takimiya K., Kunugi Y., and Otsubo T. Chem. Lett. 36 (2007) 578
4. Laquindanum J.G., Katz H.E., and Lovinger A.J. J. Am. Chem. Soc. 120 (1998) 664
5. Katz H.E., and Bao Z. J. Phys. Chem. B 104 (2000) 671
6. Takimiya K., Ebata H., Sakamoto K., Izawa T., Otsubo T., and Kunugi Y. J. Am. Chem. Soc. 128 (2006) 12604
7. Yamamoto K., and Takimiya K. J. Am. Chem. Soc. 129 (2007) 2224
8. Pietrangelo A., MacLachlan M.J., Wolf M.O., and Patrick B.O. Org. Lett. 9 (2007) 3571
9. Tilak B.D. Proc. Indian Acad. Sci. Sect. A 33 (1951) 71
10. Tilak B.D. Proc. Indian Acad. Sci. Sect. A 37 (1953) 114
11. Tilak B.D. Tetrahedron 9 (1960) 76
12. Muller D., Muller J.-F., and Cagniant D. J. Chem. Res. (S) (1977) 328
13. For some examples of the formation of the thiophene-based aromatic compounds by FVP, see:
14. Leow M.L., and MacBride J.A.H. Tetrahedron Lett. 25 (1984) 4283
15. Aitken R.A., Boeters C., and Morrison J.J. J. Chem. Soc. Perkin Trans. 1 (1997) 2625
16. Imamura K., Hirayama D., Yoshimura H., Takimiya K., Aso Y., and Otsubo T. Tetrahedron Lett. 40 (1999) 2789
17. Ibrahim Y.A., Al-Awadi N.A., and Kaul K. Tetrahedron 57 (2001) 7377
18. Brown A., Cadogan J.I.G., MacPherson A.D., and McNab H. ARKIVOC xi (2007) 64
19. Sonoda M., Itahashi K., and Tobe Y. Tetrahedron Lett. 43 (2002) 5269
20. Rahman S.M.A., Sonoda M., Itahashi K., and Tobe Y. Org. Lett. 5 (2003) 3411
21. Rahman S.M.A., Sonoda M., Ono M., Miki K., and Tobe Y. Org. Lett. 8 (2006) 1197
22. Scott L.T. Angew. Chem. Int. Ed. 43 (2004) 4994
23. Frisch M.J., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M.A., Cheeseman J.R., Montgomery Jr. J.A., Vreven T., Kudin K.N., Burant J.C., Millam J.M., Iyengar S.S., Tomasi J., Barone V., Mennucci B., Cossi M., Scalmani G., Rega N., Petersson G.A., Nakatsuji H., Hada M., Ehara M., Toyota K., Fukuda R., Hasegawa J., Ishida M., Nakajima T., Honda Y., Kitao O., Nakai H., Klene M., Li X., Knox J.E., Hratchian H.P., Cross J.B., Bakken V., Adamo C., Jaramillo J., Gomperts R., Stratmann R.E., Yazyev O., Austin A.J., Cammi R., Pomelli C., Ochterski J.W., Ayala P.Y., Morokuma K., Voth G.A., Salvador P., Dannenberg J.J., Zakrzewski V.G., Dapprich S., Daniels A.D., Strain M.C., Farkas O., Malick D.K., Rabuck A.D., Raghavachari K., Foresman J.B., Ortiz J.V., Cui Q., Baboul A.G., Clifford S., Cioslowski J., Stefanov B.B., Liu G., Liashenko A., Piskorz P., Komaromi I., Martin R.L., Fox D.J., Keith T., Al-Laham M.A., Peng C.Y., Nanayakkara A., Challacombe M., Gill P.M.W., Johnson B., Chen W., Wong M.W., Gonzalez C., and Pople J.A. Gaussian 03, Revision D.01 (2005), Gaussian, Inc., Wallingford, CT