Neighboring group participation by heteroaromatic rings: The Wagner- Meerwein type skeletal rearrangement in the electrophilic addition reactions of norbornadiene-fused furans, pyrroles, and thiophenes

Bulletin of the Chemical Society of Japan

Volumn 72, Issue 7, 1999, Pages 1597-1605

  Kobayashi, Tomoshige ^a   Tsuzuki, Takeo ^a   Saitoh, Mayu ^a  

^a SHINSHU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BROMINE DERIVATIVE; CHLORIDE; FURAN DERIVATIVE; HETEROCYCLIC COMPOUND; PYRROLE DERIVATIVE; THIOPHENE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; MOLECULAR DYNAMICS; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0032766769     PISSN: 00092673     EISSN: None     Source Type: Journal    
DOI: 10.1246/bcsj.72.1597     Document Type: Article

References (36)

1. J. March, "Advanced Organic Chemistry," Wiley-Interscience, New York, Chichester, Brishbane, Toronto, and Singapore (1985), pp. 277 and 612.
2. M. B. Smith, "Organic Synthesis," McGraw-Hill, Inc., New York, St. Louis, San Francisco, Auckland, Bogotá, Caracas, Lisbon, London, Madrid, Mexico City, Milan, Montreal, New Delhi, San Juan, Singapore, Sydney, Tokyo, and Toronto (1994), pp. 266, 274, and 580.
3. P. Vogel, "Carbocation Chemistry," Elsevier, Amsterdam, Oxford, New York, and Tokyo (1985), Chap. 7.8.2, p. 267.
4. G. Wittig and E. Knauss, Chem. Ber., 91, 895 (1958).
5. J. W. Wilt, G. Gutman, W. J. Ranus, Jr., and A. R. Zigman, J. Org. Chem., 32, 893 (1967).
6. S. J. Cristol and G. W. Nachtigall, J. Org. Chem., 32, 3727 (1967).
7. A. Daştan, Ü. Demir, and M. Balci, J. Org. Chem., 59, 6534 (1994).
8. W. Adam, O. D. Lucchi, and I. Erden, Angew. Chem., Int. Ed. Engl., 18, 468 (1979).
9. N. S. Zefirov, N. K. Sadovaya, L. A. Novgorodtseva, and I. V. Bodrikov, Tetrahedron, 34, 1373 (1978).
10. N. S. Zefirov, N. K. Sadovaya, L. A. Novgorodtseva, R. S. Achemedova, S. V. Baranov, and I. V. Bodrikov, Tetrahedron, 35, 2759 (1979).
11. V. N. Ermolaeva, N. K. Sadovaya, and N. S. Zefirov, Zh. Org. Khim., 17, 1554 (1981).
12. G. A. Olah and G. Liang, J. Am. Chem. Soc., 97, 2236 (1975).
13. G. A. Olah and G. Liang, J. Am. Chem. Soc., 98, 6304 (1976).
14. V. A. Bushmelev, V. P. Vetchinov, A. M. Genaev, V. I. Mamatyuk, and V. G. Shubin, Mendeleev Commun., 1996, 187.
15. G. K. S. Prakash, L. Ohannesian, M. Arvanaghi, and G. A. Olah, Gazz. Chim. Ital., 117, 213 (1987).
16. H. Vančik, A. M. Genaev, and V. G. Shubin, J. Chem. Soc., Perkin Trans. 2, 1997, 667.
17. H. Tanida, T. Irie, and Y. Hayashi. J. Org. Chem., 49, 2527 (1984).
18. H. Tanida, T. Irie, and Y. Hayashi, J. Org. Chem., 50, 821 (1985).
19. H. Tanida and T. Irie, J. Org. Chem., 52, 5218 (1987).
20. R. G. Cooks, R. N. McDonald, P. T. Cranor, H. E. Petty, and N. L. Wolfe, J. Org. Chem., 38, 1114 (1973).
21. T. Kobayashi, K. Ono, H. Suda, Y. Yamashita, and H. Kato, Bull. Chem. Soc. Jpn., 66, 2707 (1993).
22. T. Kobayashi, H. Fujieda, Y. Murakami, T. Nakamura, K. Ono, S. Yamamoto, and H. Kato, Bull. Chem. Soc. Jpn., 67, 3082 (1994).
23. T. Kobayashi, H. Suda, H. Takase, R. Iriye, and H. Kato, Bull. Chem. Soc. Jpn., 68, 3269 (1995).
24. T. Kobayashi, S. Yamamoto, and H. Kato, Bull. Chem. Soc. Jpn., 70, 1193 (1997).
25. T. Kobayashi, H. Sugawara, and B. Nikaeen, Bull. Chem. Soc. Jpn., 71, 497 (1998).
26. T. Kobayashi, Yuki Gosei Kagaku Kyoukai Shi (J. Synth. Org. Chem. Jpn.), 56, 192 (1998).
27. T. Kobayashi and K. Miki, Bull. Chem. Soc. Jpn., 71, 1443 (1998).
28. H. Wynberg and A. J. H. Klunder, Recl. Trav. Chim. Pays-Bas, 88, 328 (1969).
29. J. de-Wit and H. Wynberg, Tetrahedron, 29, 1379 (1973).
30. S. F. Nelsen and D. L. Kapp, J. Am. Chem. Soc., 107, 5548 (1985).
31. Calculated with "MacSpartan Plus Ver. 1.2," Wavefunction, Inc., Irvine, California, U.S.A.
32. K. P. C. Vollhardt, Synthesis, 1975, 765.
33. H.-D. Scharfand W. Küsters, Chem. Ber., 105, 564 (1972).
34. Y. Miyahara, J. Heterocycl. Chem., 16, 1147 (1979).
35. M. B. Hursthouse, K. M. A. Malik, D. E. Hibbs, S. M. Roberts, A. J. H. Seago, V. Šik, and R. Storer, J. Chem. Soc., Perkin Trans. 1, 1995, 2419.
36. R. C. Cookson, S. S. Gupte, I. D. R. Stevens, and C. T. Watts, Org. Synth., Coll. Vol. VI, 936 (1988).