The 2-oxocyclopentanecarboxylic acid keto-enol system in aqueous solution: Generation of the enol by hydration of an acylketene

Y Chiang, AJ Kresge, VA Nikolaev…

文献索引：Chiang; Kresge; Nikolaev; Popik Journal of the American Chemical Society, 1997 , vol. 119, # 46 p. 11183 - 11190

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被引用次数: 13

摘要

Flash photolysis of 2-diazocyclohexane-1, 3-dione in aqueous solution produced 2- ketocyclopentylideneketene, which hydrated to the enol of 2-oxocyclopentanecarboxylic acid, and the enol then isomerized to the keto form of the acid. This ketene proved to be a remarkably reactive substance, with an uncatalyzed hydration rate constant of k= 1.4× 106 s- 1 and a hydroxide-ion-catalyzed rate constant of 7.5× 107 M-1 s-1; no acid catalysis of ...