Collect. Czech. Chem. Commun. 2004, 69, 1325-1344

Concave Reagents. New 2'-Substituted m-Terphenyls

Michael Abbassa, Christine Kühlb, Christian Mantheyc, Anja Müllerd and Ulrich Lüninge,*

a ChemCon GmbH, Engesserstrasse 4b, D-79108 Freiburg, Germany
b Bernina Biosystems GmbH, Am Klopferspitz 19a, D-82152 Martinsried, Germany
c ipal Gesellschaft für Patentverwertung Berlin mbH, Bundesallee 210, D-10719 Berlin, Germany
d Gilson International BV, Otto-Hahn-Str. 17, D-65520 Bad Camberg, Germany
e Institut für Organische Chemie, Olshausenstr. 3/4, D-24098 Kiel, Germany


New 2'-substituted 2,2'',6,6''-tetramethyl-1,1':3',1''-terphenyls have been synthesized. Solubility of concave acids 4b-6b could be enhanced by substitution in 4 and 4'' position, allowing the study of hydrogen-bonded heterodimers. Concave acids show larger binding constants for 2-amidopyridines 7 than non-macrocyclic ones, probably due to the prevention of homodimer formation by the macrocyclic shielding. New 2,6-diarylbenzyl alcohols 1d, 8d and 9d have been synthesized and tested in protonation reactions. New functional groups were introduced into the 2' position: OH (phenols 1f and 12f) and NH2 (aniline 1j). The basicity of aniline 1j in ethanol was determined by titration and was compared to other bases. Also sulfonic acids 1l and 17l were prepared, and the corresponding methyl esters 1m and 17m were tested as methylating agents.

Keywords: Arenes; Biaryls; Terphenyls; Phenols; Sulfonic acids; Receptors; Basicity; Hydrogen bonds; Macrocycles; Supramolecular chemistry.

References: 49 live references.