The Mills-Nixon effect. III. Detritiation of veratrol, 1,3-benzodioxole, and 1,4-benzodioxan

Abstract

The rates of detritiation of [3-T]- and [4-T]-veratrol, [4-T]- and [5-T]-1,3-benzodioxole, and [5-T]- and [6-T]-1,4-benzodioxan have been measured at 30º in anhydrous trifluoroacetic acid. The observed order of reactivities can be explained in terms of a balance of strain and hybridization effects imposed by the fused ether rings, and differences in the extent of Ar-O delocalization among the three substrates.