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

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.