Abstract
(Kenyon and Mason (J. Chem. Soc. , 1952, 4684), attempting to prepare the sulphone from p-tolyl trimethoxydiphenylmethyl sulphide by oxidation with paracotic acid, obtained instead the unexpected 2:6-dimethoxy-l: 4-benzoquinone. This apparently anomalous reaction stimulated this research into the behaviour of other aromatic compounds when acted upon by peracetic acid : a number of compounds, the majority being phenolic ethers, have been studied in this respect. In some cases, no reaction was observed; in others, the compound underwent ring-cleavage and produced a complex mixture of aliphatic residues; in many cases, however, the aromatic ring survived in the quinonoid form, e. g., [chemical formula]. The likely reaction mechanisms involved in this type of oxidation are discussed.