Reactions of the free toluene-p-sulphonyl radical. Part II. Reactions with polycyclic aromatic hydrocarbons
Abstract
Toluene-p-sulphonyl iodide, in the presence of copper powder, adds p·Me·C6H4·SO2· radicals to the meso-positions of both anthracene and 2,3-benzanthracene: there is no reaction with phenanthrene or 1,2-benzanthracene. In the absence of copper some meso-substitution of anthracene also occurs. With both 9-methyl and 9,10-dimethyl-anthracene side-chain substitution of hydrogen by p·Me·C6H4·SO2· occurs at a meso-methyl group. These reactions are interpreted in relation to the partial polar character of toluene-p-sulphonyl free radicals.