Reactions of 1,2,3-benzothiadiazole with phenyl and with methyl radicals

Abstract

The reaction of 1,2,3-benzothiadiazole (I) with phenyl radicals, at room temperature, afforded diphenyl sulphide, dibenzothiophen, thianthren, 4-phenylthiodibenzothiophen, and 1,2-bisphenylthiobenzene. Similarly the reaction of (I) with methyl radicals gave thioanisole, thianthren, 4-methylthiodibenzothiophen, and 1-methylthio-2-phenylthiobenzene. A mechanism is proposed which assumes initial attack of phenyl or methyl radical at the sulphur atom of (I) to give o-phenylthio-(X) or o-methylthio-phenyl radical.