Syntheses and Properties of Extremely Stable Di(1-azulenyl)phenylmethyl and (1-Azulenyl)diphenylmethyl Cations Having Dimethylamino Substituents on Their Phenyl Groups

Bulletin of the Chemical Society of Japan

Volumn 69, Issue 11, 1996, Pages 3225-3237

  Ito, Shunji ^a   Kobayashi, Hiroki ^a   Kikuchi, Shigeru ^a   Morita, Noboru ^a   Asao, Toyonobu ^b  

^a TOHOKU UNIVERSITY   (Japan)

^b IWATE UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001065215     PISSN: 00092673     EISSN: None     Source Type: Journal    
DOI: 10.1246/bcsj.69.3225     Document Type: Article

References (25)

1. a) S. Ito, N. Morita, and T. Asao, Tetrahedron Lett., 32, 773 (1991)
2. b) S. Ito, N. Morita, and T. Asao, Tetrahedron Lett., 35, 751 (1994)
3. c) S. Ito, N. Morita, and T. Asao, Bull. Chem. Soc. Jpn., 68, 1409 (1995)
4. d) S. Ito, N. Morita, and T. Asao, Tetrahedron Lett., 35, 3723 (1994)
5. e) S. Ito, N. Morita, and T. Asao, Bull. Chem. Soc. Jpn., 68, 2011 (1995)
6. f) S. Ito, N. Morita, and T. Asao, Bull. Chem. Soc. Jpn., 68, 2639 (1995)
7. g) S. Ito, M. Fujita, N. Morita, and T. Asao, Chem. Lett., 1995, 475
8. h) S. Ito, M. Fujita, N. Morita, and T. Asao, Bull. Chem. Soc. Jpn., 68, 3611 (1995)
9. i) S. Ito, S. Kikuchi, N. Morita, and T. Asao, Chem. Lett., 1996, 175
10. j) T. Asao and S. Ito, J. Synth. Org. Chem., 54, 2 (1996).
11. E. M. Arnett and R. D. Bushick, J. Am. Chem. Soc., 86, 1564 (1964).
12. R+ value of tris[4-(dimethylamino)-phenyl]methyl cation is fairly larger than that of triphenylmethyl cation (1) : a) R. J. Goldacre and J. N. Phillips, J. Chem. Soc., 1949, 1724; b) N. C. Deno and A. Schriesheim, J. Am. Chem. Soc., 77, 3051 (1955).
13. R+ value of tris[4-(dimethylamino)-phenyl]methyl cation is fairly larger than that of triphenylmethyl cation (1) : a) R. J. Goldacre and J. N. Phillips, J. Chem. Soc., 1949, 1724; b) N. C. Deno and A. Schriesheim, J. Am. Chem. Soc., 77, 3051 (1955).
14. F. Gerson, G. Plattner, and Z. Yoshida, Mol. Phys., 21, 1027 (1971).
15. K. Deuchert and S. Hünig, Angew. Chem., Int. Ed. Engl., 17, 875 (1978).
16. a) R. C. Kerber and H. M. Hsu, J. Am. Chem. Soc., 95, 3239 (1973)
17. b) K. Komatsu, K. Masumoto, Y. Waki, and K. Okamoto, Bull. Chem. Soc. Jpn., 55, 2470 (1982).
18. The absorption maxima of 5a-c and 6a-c are rather comparable with that of tris[4-(dimethylamino)phenyl]methyl cation (590 nm (log ε 4.95)) : N. C. Deno and A. Schriesheim, J. Am. Chem. Soc., 77, 3044 (1955).
19. a) S. Ito, N. Morita, and T. Asao, Tetrahedron Lett., 33, 6669 (1992)
20. b) S. Ito, N. Monta, and T. Asao, Chem. Lett., 1994, 477.
21. H. Bock, K. Ruppert, K. Merzweiler, D. Fenske, and H. Goesmann, Angew. Chem., Int. Ed. Engl., 28, 1684 (1989).
22. a) T. K. Alice and M. Sundaralingam, J. Am. Chem. Soc., 94, 1688 (1972)
23. b) G. R. Clark, P. W. J. Surman, and M. J. Taylor, J. Chem. Soc., Faraday Trans., 91, 1523 (1995).
24. E. Oeser, Chem. Ber., 107, 627 (1974).
25. K. Mislow, Acc. Chem. Res., 9, 26 (1976).