Abstract
Rate factors for the detritiation of triptycene, 9,10-dihydroanthracene, and o-xylene by anhydrous trifluoroacetic acid at 70° have been obtained as follows: f1tript., 51; f2tript., 362; f19,10-dihy., 444; f29,10-dihy., 650; f3o-xyl., 1335; f4o-xyl., 1895. It is shown that for triptycene the reactivity of the 1-position is considerably less, and that of the 2-position slightly greater, than predicted from the xylene and 9,10-dihydroanthracene data. These results are very satisfactorily accounted for by a theory recently advanced to explain the Mills–Nixon effect. In the light of this theory it is considered that transannular stabilisation of the electron-deficient transition states for substitution in triptycene is probably negligible.
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