Some observations relating to substituent effects in halogenation. Part VIII. The kinetics and reactions of indane, 9,10-dihydroanthracene, and tetralin with chlorine acetate in aqueous acetic acid

Abstract

Rates of chlorination of 9,10-dihydroanthracene, indane, and tetralin with chlorine acetate and its protonated form in aqueous acetic acid at 25° have been examined and the product obtained determined by g.l.c. The partial rate factors have been calculated. The reactivity decreases in the order tetralin > 9,10-dihydroanthracene > indane. α-Aryl reactivities fallow the same trend. The α : β reactivity ratios found for these compounds confirm earlier results found for nitration, bromination, and tritiation and which were explained by a combination of strain and hybridization effects. The α-aryl position in all these compounds show enhanced reactivity in the presence of catalytic amounts of mineral acid, this being particularly shown by the α-position in indane.