Ketonization of the remarkably strongly acidic elongated enol generated by flash photolytic decarboxylation of p-benzoylphenylacetic acid in aqueous solution

Chemical Communications

Volumn , Issue 33, 2005, Pages 4231-4233

  Chiang, Yvonne ^a   Kresge, A Jerry ^a   Onyido, Ikenna ^a   Richard, John P ^b   Wan, Peter ^c   Xu, Musheng ^c  

^a UNIVERSITY OF TORONTO   (Canada)

^b UNIVERSITY AT BUFFALO   (United States)

^c UNIVERSITY OF VICTORIA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

4 BENZOYLPHENYLACETIC ACID; ACETIC ACID DERIVATIVE; ALCOHOL DERIVATIVE; UNCLASSIFIED DRUG;

ACIDITY; ARTICLE; CHEMICAL REACTION; DECARBOXYLATION; KETONIZATION; PHOTOLYSIS;

EID: 25144435367     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b506706e     Document Type: Article

References (13)

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5. See supporting information.
6. In perchloric acid solutions the absorbance from the transient species of interest here diminished as the acid concentration increased, consistent with decarboxylation occurring through the carboxylate ion form of the substrate, and HPLC analysis showed the formation of other (uninvestigated) products. These interferences could be diminished somewhat by using deoxygenated solutions and accumulating data from several replicate flash photolysis shots.
7. J. R. Keeffe and A. J. Kresge, in The Chemistry of Enols, ed. Z. Rappoport, Wiley, New York, 1990, ch. 7.
8. The symbol "L" is used to denote either protium or deuterium, whereas "H" is used specifically for protium and "D" for deuterium.
9. This is a concentration equilibrium constant applicable at the ionic strength, 0.10 M, of the solutions in which it was determined.
10. A. J. Kresge, R. A. More O'Ferrall and M. F. Powell, in Isotopes in Organic Chemistry, ed. E. Buncel and C. C. Lee, Elsevier, Amsterdam, 1987, vol. 7, ch. 4.
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