Synthesis and properties of stabilized bis(2-oxo-2H-cyclohepta[b]-furan-3-yl)phenylmethyl and bis(1,2-dihydro-2-oxo-N-phenylcyclohepta[b]pyrrol-3-yl)phenylmethyl cations and their derivatives: Remarkable substituent effect on the conformation and stability of the cations

Journal of the Chemical Society. Perkin Transactions 2

Volumn , Issue 12, 2000, Pages 2427-2435

  Naya, Shin Ichi ^a   Nitta, Makoto ^a  

^a WASEDA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CONFORMATIONS; ELECTROCHEMISTRY; IONS; OXIDATION; PHASE TRANSITIONS; REDUCTION; SPECTROPHOTOMETRY; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

BENZALDEHYDE; CONFORMATION CHANGE; ELECTROCHEMICAL REDUCTION; HAMMETT EQUATION;

AROMATIC COMPOUNDS;

EID: 0034587287     PISSN: 03009580     EISSN: None     Source Type: Journal    
DOI: 10.1039/b006752k     Document Type: Article

References (31)

1. S. Ito, N. Morita and T. Asao, Tetrahedron Lett., 1991, 32, 773.
2. Synthesis of the tris(4,6,8-trimethylazulen-1-yl)methyl cation is previously reported, K. Hafner, H. Pelster and J. Schneider, Liebigs Ann. Chem., 1961, 650, 62.
3. S. Ito, N. Morito and T. Asao, Tetrahedron Lett., 1994, 35, 751.
4. S. Ito, N. Morita and T. Asao, Tetrahedron Lett., 1994, 35, 3723.
5. S. Ito, N. Morito and T. Asao, Bull. Chem. Soc. Jpn., 1995, 68, 1409.
6. S. Ito, N. Morita and T. Asao, Bull. Chem. Soc. Jpn., 1995, 68, 2011
7. S. Ito, N. Morita and T. Asao, Bull. Chem. Soc., Jpn., 1995, 68, 2639.
8. S. Ito, S. Kikuchi, N. Morita and T. Asao, Bull. Chem. Soc. Jpn., 1999, 72, 839.
9. S. Ito, S. Kikuchi, N. Morita and T. Asao, J. Org. Chem., 1999, 64, 5815.
10. S. Ito, M. Fujita, N. Morita and T. Asao, Chem. Lett., 1995, 475.
11. S. Ito, M. Fujita, N. Morita and T. Asao, Bull. Chem. Soc. Jpn., 1995, 68, 3611.
12. S. Ito, H. Kobayashi, S. Kikuchi, N. Morita and T. Asao, Bull. Chem. Soc. Jpn., 1996, 69, 3225.
13. S. Ito, S. Kikuchi, H. Kobayashi, N. Morita, and T. Asao, J. Org. Chem., 1997, 62, 2423.
14. S. Seto, Sci. Rep. Tohoku Univ., Ser. 1, 1953, 37, 367.
15. M. Nitta and S. Naya, J. Chem. Res. (S), 1998, 522.
16. M. Nitta and S. Naya, J. Chem. Res. (M), 1998, 2263.
17. R.W. Alder and C. Wilshire, J. Chem. Soc., Perkin Trans. 2, 1975, 1464
18. T. Nozoe, T. Toda, T. Asao and A. Yamanouchi, Bull. Chem. Soc. Jpn., 1968, 41, 2935.
19. N. Abe and T. Takehiro, Chem. Lett., 1987, 1727
20. N. Abe and T. Takehiro, Bull. Chem. Soc. Jpn., 1988, 61, 1225.
21. S. Naya and M. Nitta, J. Chem. Soc., Perkin. Trans. 1, 2000, 2777.
22. E.M. Arnett and R.D. Bushick, J. Am. Chem. Soc., 1964, 86, 1564.
23. M.J.S. Dewar, E.G. Zoebisch, E.F. Healy and J.J.P. Stewart, J. Am. Chem. Soc., 1985, 107, 3902
24. M.J.S. Dewar and E.G. Zoebisch, THEOCHEM, 1988, 180, 1.
25. C.D. Ritchie, W.F. Sager and E.S. Lewis, J. Am. Chem. Soc., 1962, 84, 2349.
26. S. Lovell, B.J. Marquardt and B. Kahr, J. Chem. Soc., Perkin. Trans. 2, 1999, 2241.
27. H.H. Freedman, in Carbonium Ions, eds. G. A. Olah and P. v. R. Schleyer, Wiley-Interscience, New York, 1973.
28. H.G. Viehe, R. Merényi, L. Stella and Z. Janousek, Angew. Chem., Int. Ed. Engl., 1979, 18, 917, and references cited therein..
29. K. Okamoto, K. Takeuchi, K. Komatsu, Y. Kubota, R. Ohara, M. Arima, K. Takahashi, Y. Waki and S. Shirai, Tetrahedron, 39, 4011, and references cited therein.
30. C. Hansch, A. Leo and R.W. Taft, Chem. Rev., 1991, 91, 165.
31. J. Griffiths and K.J. Pender, Dyes Pigm., 1981, 2, 37.