The hydrolysis of 4-acyloxy-4-substituted-2, 5-cyclohexadienones: Limitations of aryloxenium ion chemistry

M Novak, SA Glover

Index: Novak, Michael; Glover, Stephen A. Journal of the American Chemical Society, 2005 , vol. 127, # 22 p. 8090 - 8097

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Citation Number: 20

Abstract

The title compounds serve as potential precursors to aryloxenium ions, often proposed, but primarily uncharacterized intermediates in phenol oxidations. The uncatalyzed and acid- catalyzed decomposition of 4-acetoxy-4-phenyl-2, 5-cyclohexadienone, 2a, generates the quinol, 3a. 18O-Labeling studies performed in 18O-H2O, and monitored by LC/MS and 13C NMR spectroscopy that can detect 18O-induced chemical shifts on 13C resonances, show ...