Protonation and acid catalysed hydrolysis of nitrosoaryl ethers

Abstract

Studies of the equilibrium protonation and kinetics of acid catalysed hydrolysis of 4-nitrosoanisole, 4-nitrosophenyl phenyl ether and related compounds in dilute aqueous acid and in concentrated aqueous trifluoroacetic acid are reported. Hydrolysis is remarkably facile and occurs by nucleophilic attack of water at the ring carbon bearing the alkoxy or aryloxy substituent of the protonated nitroso aromatic. Direct and indirect pK_a determinations for nitroso protonation are reported.