Synthesis of 2,3-disubstituted norbornadienes

Canadian Journal of Chemistry

Volumn 78, Issue 5, 2000, Pages 527-535

  Tranmer, Geoffrey K ^a   Yip, Carol ^a   Handerson, Sean ^a   Jordan, Robert W ^a   William, Tam ^a  

^a UNIVERSITY OF GUELPH   (Canada)

Author keywords

2,3 disubstituted norbornadienes; Diels Alder reaction; Lithium halide exchange

Indexed keywords

2,3 DIBROMONORBORNADIENE; HALIDE; LITHIUM; NORBORNADIENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033918041     PISSN: 00084042     EISSN: None     Source Type: Journal    
DOI: 10.1139/v00-047     Document Type: Article

References (27)

1. 1. C. Yip, S. Handerson, R. Jordan, and W. Tam. Org. Lett. 1, 791 (1999).
2. 2. H.L. Holmes. Org. React. 4, 60 (1948).
3. 3. B.M. Trost, I. Fleming, and L.A. Paquette. Comprehensive organic synthesis. Vol. 5. Pergamon, Oxford. 1991. Chap. 4.1.
4. 4. K. Ishihara, S. Kondo, H. Kurihara, and H. Yamamoto. J. Org. Chem. 62, 3026 (1997), and refs. therein.
5. 5. E.J. Corey and T.W. Lee. Tetrahedron Lett. 38, 5755 (1997), and refs. therein.
6. 6. T. Nishikubo, A. Kameyama, K. Kishi, and Y. Mochizuki. J. Polym. Sci. Part A: Polym. Chem. 32, 2765 (1994), and refs. therein.
7. 7. E.J. Corey, M. Shibasaki, K.C. Nicolaou, C.L. Malmsten, and B. Samuelesson. Tetrahedron Lett. 737 (1976).
8. 8. M. Lee, I. Ikeda, T. Kawabe, S. Mori, and K. Kanematsu. J. Org. Chem. 61, 3406 (1996).
9. 9. K. Sato, O. Miyamoto, S. Inoue, and K. Honda. Chem. Lett. 1183 (1981).
10. 10. H. Monti, C. Corriol, and M. Bertrand. Tetrahedron Lett. 23, 5539 (1982).
11. 11. W.G. Dauben and R.L. Cargill. Tetrahedron, 15, 197 (1961).
12. 12. G.S. Hammond, N.J. Turro, and A. Fisher. J. Am. Chem. Soc. 83, 4674 (1961).
13. 13. N.J. Turro, W.R. Cherry, M.F. Manfred, and M.J. Mairbach. J. Am. Chem. Soc. 99, 7390 (1977).
14. 14. H. Tomioka, Y. Hamano, and Y. Izawa. Bull. Chem. Soc. Jpn. 60, 821 (1987).
15. 15. E.E. Bonfantini and D.L. Officer. J. Chem. Soc. Chem. Commun. 1445 (1994).
16. 16. M. Maafi, C. Lion, and J.J. Aaron. New J. Chem. 20, 559 (1996).
17. 17. V.A. Chernoivanov, A.D. Dubonosov, V.A. Bren, V.I. Minkin, A.N. Suslov, and G.S. Borodkin. Mol. Cryst. Liq. Cryst. 297, 239 (1997).
18. 18. M. Stäble, R. Lehmann, J. Kramaø, and M. Schlosser. Chimia, 39, 229 (1985).
19. 19. H.D. Verkruijsse and L. Brandsma. Recl. Trav. Chim. Pays-Bas, 105, 66 (1986).
20. 20. J. Kenndoff, K. Polborn, and G. Szeimies. J. Am. Chem. Soc. 112, 6117 (1990).
21. 21. P.G. Gassman and I. Gennick. J. Am. Chem. Soc. 102, 6864 (1980).
22. 22. W.J. Scott and J.K. Stille. J. Am. Chem. Soc. 108, 3033 (1986).
23. 23. V. Farina, V. Krishnamurthy, and W.J. Scott. Org. React. 50, 1 (1997).
24. 24. N. Miyaura and A. Suzuki. Chem. Rev. 95, 2457 (1995).
25. 25. R.F. Heck. In Comprehensive organic synthesis. Vol. 4. Edited by B.M. Trost and I. Fleming. Pergamon Press, New York. 1991. pp. 883-863.
26. 26. K. Sonogashira. In Comprehensive organic synthesis. Vol. 3. Edited by B.M. Trost and I. Fleming. Pergamon Press, New York. 1991. pp. 521-549.
27. 27. W.C. Still, M. Kahn, and A. Mitra. J. Org. Chem. 43, 2923 (1978).