On the dealkylation of aromatic ethers with nitrous acid
Abstract
Monoethers of hydroquinone and of catechol, in which the aromatic hydrogen atoms are hindered towards electrophilic substitution by bulky substituents, are smoothly converted into the corresponding quinones and alcohols on treatment with nitrous acid. The mechanism of this reaction has been elucidated with the aid of appropriate 18O-labelled compounds. In certain cases dialkyl ethers are similarly converted into quinones by nitrous acid. The mild conditions needed for these dealkylations makes the method of potential value for compounds with the appropriate substitution pattern.