Is benzene oxide homoaromatic? A microcalorimetric study

ZS Jia, P Brandt, A Thibblin

Index: Jia; Brandt; Thibblin Journal of the American Chemical Society, 2001 , vol. 123, # 42 p. 10147 - 10152

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Citation Number: 13

Abstract

Rate constants and heats of reaction for the aromatization of benzene oxide (1) and the acid- catalyzed aromatization of benzene hydrate (2) in highly aqueous solution giving phenol and benzene, respectively, have been measured by heat-flow microcalorimetry. The measured heat of reaction of benzene oxide, Δ H=-57.0 kcal mol-1, is much larger than that of benzene hydrate, Δ H=-38.7 kcal mol-1, despite an unusually low reactivity of benzene ...