Abstract
Abstract The alkaline fusion of 2-chlorophenyl phenyl sulfone afforded phenol, benzene and chlorobenzene. The initial step of the reaction appears to be the aromatic SN2-type replacement of chlorine to form 2-hydroxyphenyl phenyl sulfone upon which the hydroxide ion further attacks both phenyl carbon-1 and the sulfur atom of the sulfone group to form the final products. The 14C tracer experiment indicates that the preference of the nucleophilic-attacking site of the hydroxide ion appears to vary with the reaction temperature. A similar alkaline fusion of 2-bromo-4-tolyl phenyl sulfone gave not only benzene, bromotoluene, and phenol, but also o- and m-cresol, indicating that the reaction proceeds through a somewhat different path. Meanwhile, the alkaline fusion of 2-chlorobenzenesulfinic acid appears to proceed through the o-sulfinic benzyne formation; thus 2-bromo-4-tolylsulfinic acid gave equal amounts of o- and m-cresols.
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