309933-96-8Relevant academic research and scientific papers
peri-Naphthylenediamines 32 *. Reactions of 4,5-bis(dimethylamino)-1-naphthyllithium and 4,5-bis(dimethylamino)-1-naphthylmagnesium bromide with electrophilic agents. New representatives of double naphthalene "proton sponges" with the structures of 1,1′-binaphthyl ketone and 1,1′-binaphthylmethanol
Ryabtsova,Pozharskii,Ozeryanskii,Vistorobskii
, p. 854 - 859 (2001)
The 4-deuterio, 4-methyl, 4-iodo, 4-methylthio, 4-trimethylsilyl, and 4-ethoxycarbonyl derivatives of 1,8-bis(dimethylamino)naphthalene ("proton sponge") and some related alcohols were prepared by the reactions of 4,5-bis(dimethylamino)-1-naphthyllithium or 4,5-bis(dimethylamino)-1-naphthylmagnesium bromide with the corresponding electrophilic reagents. New representatives of double "proton sponges" with the structures of 1,1′-binaphthyl ketone and 1,1′-binaphthylmethanol were synthesized. The pKa values of selected compounds in DMSO were measured by competitive protonation.
peri-Naphthalelnediamines. 27. Transformations of tertiary carbocations stabilized by the 4,5-bis(dimethylamino)-1-naphthyl group
Pozharskii, A. F.,Ryabtsova, O. V.,Vistorobskii, N. V.,Starikova, Z. A.
, p. 1097 - 1102 (2007/10/03)
Tertiary alcohols containing the 4,5-bis(dimethylamino)-1-naphthyl group were synthesized. The carbocations that formed from α-methyl-containing alcohols in an acidic medium underwent smooth E1 elimination to give the corresponding unsaturated derivatives of the "proton sponge" in good yields. At the same time, the carbocation generated from 4-(α-hydroxybenzhydryl)-1,8-bis(dimethylamino)naphthalene was converted into a benzo-[a]fluorene derivative 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.
