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Proton sponge analogue of the Troger's base

Journal Contribution - Journal Article

Subtitle:a compound with remarkable enantiomeric stability
Proton sponge analogue of the Troger's base (4) has been obtained upon treatment of 1-amino-4,5-bis(dimethylamino)naphthalene with paraformaldehyde. It was found that in contrast to classical Troger's base 1, protonation of 4 occurs, at least thermodynamically, exclusively on peri-NMe2 groups producing a dication with two chelated [NHN](+) hydrogen bonds. This prevents the protonation of the bridge nitrogen atoms, which is responsible for rather easy racemization of 1. Indeed, two enantiomers of 4 were resolved by chiral chromatography and their much higher stability in acidic media as compared to 1 has been confirmed. Some other properties of base 4 including structure, basicity, dynamic NMR behavior, host-guest interactions and reactions with electrophiles are also discussed.
Journal: ChemistrySelect
ISSN: 2365-6549
Volume: 2
Pages: 9882 - 9887
Publication year:2017
Keywords:A1 Journal article
BOF-publication weight:1
CSS-citation score:1
Authors from:Higher Education