Generation of Benzyne in the Thermal Decomposition of 2-Carboxyphenyl p-Toluenesulfonate

Article abstract of DOI:10.1021/jo00299a022

The scope and the mechanism of the generation of 1,2-dehydrobenzene in the thermal decomposition of 2-carboxyphenyl p-toluenesulfonate and its salts (3) have been studied. 1,2-Dehydrobenzene, which can be trapped with dienic or nucleophilic reagents, is formed in a nonconcerted process with the intermediacy of a species C6H4CO2 (11) (probably benzoxet-2-one).A complex mixture of disalicylide, trisalicylide, and some other polysalicylides is formed, in the absence of trapping agents, by polymerization of this intermediate.