Af. Pozharskii et al., peri-Naphthylenediamines - 27. Transformations of tertiary carbocations stabilized by the 4,5-bis(dimethylamino)-1-naphthyl group, RUSS CHEM B, 49(6), 2000, pp. 1097-1102
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.