2‐α‐Hydroxyalkyl‐ and 2,7‐Di(α‐hydroxyalkyl)‐1,8‐bis(dimethylamino)naphthalenes: Stabilization of Nonconventional In/Out Conformers of “Proton Sponges” via N×××H—O Intramolecular Hydrogen Bonding. A Remarkable Kind of Tandem Nitrogen Inversion.

Abstract

Alcohols Q 0870 2-α-Hydroxyalkyl-and 2,7-Di(α-hydroxyalkyl)-1,8-bis(dimethylamino)naphthalenes: Stabilization of Nonconventional In/Out Conformers of "Proton Sponges" via N···H-O Intramolecular Hydrogen Bonding. A Remarkable Kind of TandemNitrogen Inversion. -A number of title compounds is prepared. The primary and secondary alcohols adopt the typical in/in conformation, whereas the tertiary alcohols exist in unconventional in/out conformation which is stabilized by N···H-O hydrogen bonding. -(POZHARSKII*, A. F.; DEGTYAREV, A. V.; RYABTSOVA, O. V.; OZERYANSKII, V. A.; KLETSKII, M. E.; STARIKOVA, Z. A.; SOBCZYK, L.; FILAROWSKI, A.; J.