Evidence for the intermediacy of an alkyne rather than an allene in the base-induced reaction of 3-bromo-6,7-benzobicyclo[3.2.11octa-2,6-diene

Tetrahedron

Volumn 55, Issue 35, 1999, Pages 10771-10778

  Tümer, Ferhan ^a   Taşkesenligil, Yavuz ^a   Balci, Metin ^b  

^a ATATÜRK UNIVERSITY   (Turkey)

^b MIDDLE EAST TECHNICAL UNIVERSITY   (Turkey)

Author keywords

[No Author keywords available]

Indexed keywords

3 BROMO 6,7 BENZOBICYCLO[3.2.1]OCTA 2,6 DIENE; ALKYNE; ALLENE DERIVATIVE; BICYCLO COMPOUND; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; PRIORITY JOURNAL; REACTION ANALYSIS; SYNTHESIS;

EID: 0033609844     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00592-X     Document Type: Article

References (21)

1. 1. (a) Johnson, R.P. Chem.Rev. 1989, 89, 1111-1124.
2. (b) Schuster, H.F., Coppola, G.M. Allenes in Organic Synthesis; John Wiley: New York, 1984.
3. (c) Landor, S.R., Ed The Chemistry of the Allene; Academic Press: New York, 1982.
4. (d) Patai, S., Ed. The Chemistry of Ketenes, Allenes and Related Compounds; Wiley: New York, 1980, Parts 1 and 2.
5. (e) Balci, M., Taşkesenligil, Y. in Advances in Strained and Interesting Organic Molecules; Halton, B., Ed; JAI: Greenwich, Vol.8., in press.
6. 2. Price, J.D.; Johnson, R.P. Tetrahedron Lett. 1986, 27, 4679-4682.
7. 3. Yildiz, Y.K.; Seçen, H.; Krawiec, M.; Watson, W.H.; Balci, M. J. Org. Chem. 1993, 58, 5355-5359.
8. 4. Balci, M.; Harmandar, M. Tetrahedron Lett. 1984, 25, 237-240.
9. 5. (a) Taşkesenligil, Y.; Kashyap, R.P.; Watson, W.H.; Balci, M. J. Org. Chem. 1993, 58, 3216-3218.
10. (b) Tümer, F.; Taşkesenligil, Y.; Daştan, A.; Balci, M. Aust. J. Chem. 1996, 49, 599-603.
11. 6. Taşkesenligil, Y.; Tümer, F.; Kazaz, C.; Balci, M. Turk. J. Chem., in press.
12. 7. Cossu, S.; De Lucchi, O.; Lucchini, V.; Valle, G.; Balci, M.; Daştan, A.; Demirci, B. Tetrahedron Lett. 1997, 38, 5319-5322.
13. 8. This compound was synthesized by an independent route starting from 2-iodobenzonorbornadiene together with 15% contamination by benzonorbornadiene: Paquette, L.A.; Bay, E.; Ku, A.Y.; Rondan, N.G.; Houk, K.N. J. Org. Chem. 1982, 47, 422-428.
14. 9. (a) Kitahonoki, K.; Takano, Y.; Matsuura, A.; Kotera, K. Tetrahedron 1969, 25, 335-353.
15. (b) Tanida, H.; Tori, K.; Kitahonoki, K. J. Am. Chem. Soc. 1967, 89, 3212-3224.
16. (c) Goldschmidt, Z.; Gutman, U. Tetrahedron 1974, 30, 3327-3331.
17. (d) Johnson, R.P.; Exarchou, A.; Jefford, C.W.; Hahn, R.C. J. Org. Chem. 1977, 42, 3758-3759.
18. 10. Wege, D. J. Org. Chem. 1990, 55, 1667-1670.
19. 11. (a) Çakmak, O.; Taşkesenligil, Y.; Balci, M. J. Org. Chem. 1991, 56, 3442-3445.
20. (b) Çakmak, O.; Balci, M.J. Org. Chem. 1989, 54, 181-187.
21. 12. Jefford, C.W.; Sweeney, A.; Delay, F. Helv. Chim. Acta 1972, 55, 2214-2227.