Journal of the American Chemical Society p. 9165 - 9171 (1995)
Update date:2022-08-02
Topics:
Chiang
Kresge
Popik
Flash photolysis of a series of arylhydroxycyclopropenones (aryl = phenyl, mesityl, 4-methoxyphenyl, 2,4,6-trimethoxyphenyl, and 1-naphthyl) in aqueous solution was found to give arylacetic acids as final products through two successively formed, short-lived reaction intermediates. Rate profiles, the form of acid-base catalysis, and solvent isotope effects identified the first of these intermediates as arylynolate ions, ArC≡CO-, and the second as arylketenes, ArCH=C=O; the identity of the ketenes was also confirmed by independent generation through photo-Wolff reaction of corresponding aryl diazo compounds. The kinetic behavior of the arylynolate ions shows that the corresponding arylynols, ArC≡COH, are remarkably strong acids, with pKa < 3.
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