Neighboring effect of pyrazole rings: Regio- and stereoselective Wagner-Meerwein rearrangement in electrophilic addition reactions of norbornadiene-fused pyrazoles

Journal of the Chemical Society, Perkin Transactions 1

Volumn , Issue 16, 2000, Pages 2731-2739

  Kobayashi, Tomoshige ^a   Uchiyama, Yosuke ^a  

^a SHINSHU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ISOMERS; REACTION KINETICS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

PYRAZOLE RINGS;

AROMATIC COMPOUNDS;

EID: 0034699198     PISSN: 14704358     EISSN: None     Source Type: Journal    
DOI: 10.1039/b002454f     Document Type: Article

References (25)

1. J. March, Advanced Organic Chemistry, Wiley-Interscience, New York, 1985, p. 277.
2. M. B. Smith, Organic Synthesis, McGraw-Hill, Inc., Tokyo, 1994, p. 266, p. 274, p. 580.
3. T. Kobayashi, Yuki Gosei Kagaku Kyokaishi, 1998, 56, 192.
4. T. Kobayashi, T. Tsuzuki and M. Saitoh, Bull. Chem. Soc. Jpn., 1999, 72, 1597.
5. T. Kobayashi, H. Sugawara and B. Nikaeen, Bull. Chem. Soc. Jpn., 1998, 71, 497.
6. T. Kobayashi and K. Miki, Bull. Chem. Soc. Jpn., 1998, 71, 1443.
7. T. Kobayashi, K. Miki, N. Behrooz and H. Baba, Tetrahedron, 1999, 55, 13179.
8. A. P. Davis and G. H. Whitham, J. Chem. Soc., Chem. Commun., 1980, 639.
9. A. Padwa and M. W. Wannamaker, J. Chem. Soc., Chem. Commun., 1987, 1742.
10. M. Yoshimatsu, M. Kawahigashi, E. Honda and T. Kataoka, J. Chem. Soc., Perkin Trans, 1, 1997, 695.
11. J. Elguero, C. Marzin, A. R. Katritzky and P. Linda, The Tautomerism of Heterocycles, Advances in Heterocyclic Chemistry Supplement 1, Academic Press, New York, 1976, Chapter 4.
12. A. N. Nesmeyanov, E. B. Zavelovich, V. N. Babin, N. S. Kochetkova and E. I. Fedin, Tetrahedron, 1975, 31, 1461.
13. A. A. Watson, D. A. House and P. J. Steel, Polyhedron, 1989, 8, 1345.
14. M. C. López, N. Jagerovice and P. Ballesteros, Tetrahedron: Asymmetry, 1994, 5, 1887.
15. H. Kotsuki, H. Hayakawa, M. Wakao, T. Shimanouchi and M. Ochi, Tetrahedron: Asymmetry, 1995, 2665.
16. H. Kotsuki, M., Wakao, H. Hayakawa, T. Shimanouchi and M. Shiro, J. Org. Chem., 1996, 61, 8915.
17. P. D. Bartlett and C. Wu, J. Org. Chem., 1984, 49, 1880.
18. W. M. Smit, N. S. Zefirov, I. V. Bodrikov and M. Z. Krimer, Acc. Chem. Res., 1979, 12, 282.
19. N. S. Zefirov, N. K. Sadovaya, L. A. Novgorodtseva and I. V. Bodrikov, Tetrahedron, 1978, 34, 1373.
20. N. S. Zefirov, N. K. Sadovaya, L. A. Novgorodtseva, R. S. Achmedova, S. V. Baranov and I. V. Bodrikov, Tetrahedron, 1979, 35, 2759.
21. V. N. Ermolaeva, N. K. Sadovaya and N. S. Zefirov Zh. Org. Khim., 1981, 17, 1554.
22. T. J. Dudley, I. P. Smoliakova and M. R. Hoffmann, J. Org. Chem., 1999, 64, 1247.
23. L. Pasquato and G. Modena, Chem. Commun., 1999, 1469.
24. Calculated with MacSpartan Plus Ver. 1.2, Wavefunction, Inc., Irvine, California, U.S.A.
25. H. Meerwein, Org. Synth., 1973, Coll. Vol. V, 1080.