The reactions of toluene and o-and p-xylene with chlorine acetate and its protonated form in aqueous acetic acid have been investigated at 25". The relative rates and product compositions determined by isotopic dilution and g.1.c. allow calculations of the partial rate factors in the various positions for the chlorinations. The values obtained for oand p-xylenes are well correlated by those obtained for the individual positions in toluene on the basis of additivity.

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Rates of chlorination of 9.1 0-dihydroanthracene, indane, and tetralin with chlorine acetate and its protonated form in aqueous acetic acid a t 25" have been examined and the product obtained determined by g.1.c. The partial rate factors have been calculated. The reactivity decreases in the order tetralin > 9.1 0-dihydroanthracene > indane. a-Aryl reactivities follow the same trend. The a : p reactivity ratios found for these compounds confirm earlier results found for nitration, bromination, and tri tiation and which were explained by a combination of strain and hybridization effects. The cc-aryl position in all these compounds show enhanced reactivity in the presence of catalytic amounts of mineral acid, this being particularly shown by the a-position in indane.

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