Detritiation in 1,8-dimethylnaphthalene, acenaphthene, and perinaphthane

Abstract

The rates of detritiation of [2-T]-, [3-T]-, and [4-T]-1,8-dimethylnaphthalene and the corresponding specifically labelled acenaphthenes and perinaphthanes have been measured a t 30° in anhydrous trifluoroacetic acid. The order of ortho and para reactivities is acenaphthene > perinaphthane > 1,8-dimethylnaphthalene; the meta positions are much less reactive in the order acenaphthene > 1,8-dimethyl- naphthalene > perinaphthane. This pattern of reactivity is discussed in terms of steric and strain effects in the transition states.