芳香族化合物に対する四酢酸鉛の反応

概要

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The reactions of lead tetraacetate with alkylaromatic compounds, acetophenone, halobenzenes, biphenyl, and anisole have been investigated. Controlled lead tetraacetate oxidation of alkylaromatic compounds offers a new method for the synthesis of substituted benzyl acetates. Acetophenone reacted at 120°C to give phenacyl acetate and phenacylidene acetate, the former being higher in yield. But neither nuclear acetoxylated nor nuclear methylated products were detected. Both chloro-benzene and bromobenzene gave nuclear acetoxylated products, the isomer distributions being, for chlorobenzene : o-, 85; m-, 5; p-, 10; and for bromobenzene: o-, 54; m-, 16; p-, 30%. Biphenyl reacted only at the reflux temperature to give acetoxybiphenyl. Anisole gave guaiacol acetate at 120°C, neither the m- and p-isomers nor the methylated products being detected.
社団法人有機合成化学協会の論文