peri-Naphthylenediamines - 27. Transformations of tertiary carbocations stabilized by the 4,5-bis(dimethylamino)-1-naphthyl group

Tertiary alcohols containing the 4,5-bis(dimethylamino)-1-naphthyl group we re synthesized. The carbocations that formed from n-methyl-containing alcoh ols in an acidic medium underwent smooth E1 elimination to give the corresp onding unsaturated derivatives of the "proton sponge" in good yields. At th e same time, the carbocation generated from 4-(alpha-hydroxybenzhydryl)-1,8 -bis(dimethylamino)naphthalene was converted into a benzo[a]fluorene deriva tive as a result of a complex reaction which has been previously unknown in the chemistry of "proton sponges." The structure of the latter derivative was established by X-ray diffraction analysis.