AQUEOUS HIGH-TEMPERATURE CHEMISTRY OF CARBOCYCLES AND HETEROCYCLES .8. AQUATHERMOLYSIS OF PARA-SUBSTITUTED PHENOLS IN THE PRESENCE AND ABSENCE OF SODIUM BISULFITE

p-Cresol and various other 4-alkyl-substituted phenols undergo dealkylation under forcing Bucherer reaction conditions (250 °C) via an oxidative free radical mechanism and do not undergo the expected heteroatom removal reaction. Products from a variety of substrates are elucidated, structures assigned, and mutually consistent reaction pathways determined. Principal reaction patterns include dealkylation, alkylation and ring closure to give benzofurans, dibenzofurans, and xanthenes. © 1990, American Chemical Society. All rights reserved.