Reaction of triaryloxonium salts with bases via dehydroarenes

Article abstract of DOI:10.1016/S0040-4039(97)00900-3

Tri-p-tolyloxonium tetrafluoroborate reacts with NaOH in water yielding a mixture of m- and p-cresls (1:1) use of MeOH as solvent rsults in a mixture of m- and p-crescols (1:1), use of MeOH as solvent results in a mixture of m- and p-methoxytoluenes (1:5:1). This result proves this reaction to proceed via 3,4-dehydrotoluene.