Non-conventional paths in electrophilic aromatic reactions. Part IX. Chlorination of hexaethylbenzene and some of its cyclic analogues

Abstract

Product analyses and kinetic studies of the chlorination in the dark of hexaethylbenzene (I), dodecahydrotriphenylene (II), and trindane (III) in acetic acid solution have shown that all three compounds undergo chlorination by a second-order process which is accompanied by extensive solvolysis. α-Substitution was ascertained in the case of compound (I). This behaviour is wholly analogous to that displayed by hexamethylbenzene. The rate-depression effects are interpreted in terms of ring strain in the transition state for compound (III) and of rigidly interlocked conformations for compound (I). Bromination in the dark is very slow.