Ketonization of (Z)-2-methoxy-1,2-diphenylvinyl alcohol. Quantitative evaluation of the remarkable kinetic stability of this enol

Canadian Journal of Chemistry

Volumn 76, Issue 9, 1998, Pages 1284-1288

  Jefferson, E A ^a   Kresge, A J ^a   Matthew, L ^a   Wu, Z ^a  

^a UNIVERSITY OF TORONTO   (Canada)

Author keywords

Enol ketonization; Enol stability; Keto enol equilibrium; phenyl and methoxy substituent effects in ketoenol systems

Indexed keywords

2 METHOXY 1,2 DIPHENYLVINYL ALCOHOL; ALCOHOL DERIVATIVE; AMMONIA; FORMIC ACID; KETONE DERIVATIVE; PERCHLORIC ACID; SODIUM HYDROXIDE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION KINETICS; ISOMER; X RAY DIFFRACTION;

EID: 0032411381     PISSN: 00084042     EISSN: None     Source Type: Journal    
DOI: 10.1139/v98-163     Document Type: Article

References (19)

1. J.F. McGarrity, A. Cretton, A.A. Pinkerton, D. Schwarzenbazch, and H.D. Flack. Angew. Chem. Int. Ed. Engl. 22, 405 (1983); Angew. Chem. Suppl. 551 (1983).
2. J.F. McGarrity, A. Cretton, A.A. Pinkerton, D. Schwarzenbazch, and H.D. Flack. Angew. Chem. Int. Ed. Engl. 22, 405 (1983); Angew. Chem. Suppl. 551 (1983).
3. H. Hart, Z. Rappoport, and S.E. Biali. In The chemistry of enols. Edited by Z. Rappoport. John Wiley & Sons, New York. 1990. Chap. 8.
4. C.D. Nenitzescu and E. Solomonica. Org. Synth. Coll. Vol. 2, 496 (1943).
5. J.R. Jones. Trans. Faraday Soc. 61, 95 (1965).
6. R.G. Bates. Determination of pH theory and practice. John Wiley and Sons, New York. 1973. p. 49.
7. J.R. Keeffe and A.J. Kresge. In The chemistry of enols. Edited by Z. Rappoport. John Wiley & Sons, New York. 1990. Chap. 7.
8. A.J. Kresge. Acc. Chem. Res. 20, 364 (1987).
9. Y. Chiang, A.J. Kresge, J.A. Santaballa, and J. Wirz. J. Am. Chem. Soc. 110, 5506 (1988).
10. Y. Chiang, A.J. Kresge, and J. Wirz. J. Am. Chem. Soc. 106, 6392 (1984).
11. Y. Chiang, A.J. Kresge, P.A. Walsh, and Y. Yin. J. Chem. Soc. Chem. Commun. 869 (1989).
12. Y. Chiang, M. Hojatti, J.R. Keeffe, A.J. Kresge, N.P. Schepp, and J. Wirz. J. Am. Chem. Soc. 109, 4000 (1987).
13. Y. Chiang, A.J. Kresge, and C.I. Young. Can. J. Chem. 56, 461 (1978).
14. A.J. Kresge, D.S. Sagatys, and H.L. Chen. J. Am. Chem. Soc. 99, 7228 (1977).
15. A.J. Kresge and M. Leibovitch. J. Org. Chem. 55, 5234 (1990).
16. J. Hine. Structural effects on equilibria in organic chemistry. John Wiley & Sons, New York. 1975. pp. 270-276.
17. K. Meyer. Justus Liebigs Ann. Chem. 380, 212 (1911).
18. J.R. Keeffe, A.J. Kresge, and N.P. Schepp. J. Am. Chem. Soc. 112, 4862 (1990).
19. J.R. Keeffe, A.J. Kresge, and J. Toullec. Can. J. Chem. 64, 1224 (1986).