High Stabilities of Di(1-azulenyl)(4-hydroxyphenyl)methyl Hexafluorophosphates and Polarized Properties of α,α-Di(1-azulenyl)-1,4-benzoquinone Methides

Journal of Organic Chemistry

Volumn 62, Issue 8, 1997, Pages 2423-2431

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

^a TOHOKU UNIVERSITY   (Japan)

^b IWATE UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001156522     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961820q     Document Type: Article

References (27)

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13. + value and in turn a higher stability of the carbocation.
14. + values of 4a were higher than that of 1a. This is in accord with these postulations.
15. (a) Goldacre, R. J.; Phillips, J. N. J. Chem. Soc. 1949, 1724-1732.
16. (b) Deno, N. C.; Schriesheim, A. J. Am. Chem. Soc. 1955, 77, 3051-3054.
17. 6 Deno, N. C.; Evans, W. L. J. Am. Chem. Soc. 1957, 79, 5804-5807.
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19. See, e.g.: (a) Zanarotti, A. Tetrahedron Lett. 1982, 23, 3815-3818. (b) Becker, H.-D. J. Org. Chem. 1967, 32,_ 2943-2047.
20. See, e.g.: (a) Zanarotti, A. Tetrahedron Lett. 1982, 23, 3815-3818. (b) Becker, H.-D. J. Org. Chem. 1967, 32,_ 2943-2047.
21. 1H NMR spectrum.
22. 11
23. + values for carbocations: (a) Kerber, R. C.; Hsu, H. M. J. Am. Chem. Soc. 1973, 95, 3239-3245. (b) Komatsu, K.; Masumoto, K.; Waki, Y.; Okamoto, K. Bull. Chem. Soc. Jpn. 1982, 55, 2470-2479.
24. + values for carbocations: (a) Kerber, R. C.; Hsu, H. M. J. Am. Chem. Soc. 1973, 95, 3239-3245. (b) Komatsu, K.; Masumoto, K.; Waki, Y.; Okamoto, K. Bull. Chem. Soc. Jpn. 1982, 55, 2470-2479.
25. a value for the protonation of acetone is reported as -7.2: Arnett, E. M. Progr. Phys. Org. Chem. 1963, 1, 223-403.
26. For interesting similar situations for solvatochromic effect of diarylquinocyclopropenes see: (a) Wellman, D. E.; West, R. J. Am. Chem. Soc. 1984, 106, 355-360. (b) West, W.; Zecher, D. C. J. Am. Chem. Soc. 1970, 92, 155-161.
27. For interesting similar situations for solvatochromic effect of diarylquinocyclopropenes see: (a) Wellman, D. E.; West, R. J. Am. Chem. Soc. 1984, 106, 355-360. (b) West, W.; Zecher, D. C. J. Am. Chem. Soc. 1970, 92, 155-161.