Anodic Oxidation of Active Methylene Groups in the Presence of Excess Carboxylic Acid

Article abstract of DOI:10.1246/bcsj.66.2767

The anodic oxidation of anthrone, (9,(10H)-anthracenone), 9,10-dihydroanthracene and 1-tetralone in acetonitrile was studied under the presence of excess carboxylic acids.The oxidation of anthrone with acetic acid gave anthraquinone, 10-acetoxyanthrone and 10-methyl-10-acetoxyanthrone.A similar reaction of anthrone with propionic acid yielded 10-propionyloxyanthrone.The electronic oxidation of 9,10-dihydroanthracene yielded anthraquinone, anthrone, and 9-acetoxyanthrone under the same conditions.Also, 1-tetralone reacted with acetic acid and propionic acid at the 4 position of the carbonyl group, giving 4-acetoxy- and 4-propionyloxy-1-tetralone, respectively.