Collect. Czech. Chem. Commun. 1999, 64, 1827-1832
https://doi.org/10.1135/cccc19991827

Regioselective Double Cyclisation of 1,2,4,5-Tetrakis(bromomethyl)benzene with Tosylated Diethylenetriamine. Towards Conformationally Biased Bis(perazacrown) Receptors

Jana Hodačováa,*, Jiří Závadaa and Peter C. Junkb

a Institute of Organic Chemistry and Biochemistry, Flemingovo nám. 2, 166 10 Prague 6, Czech Republic
b Department of Chemistry, James Cook University, Townsville, QLD, 4811, Australia

Abstract

Of three possible tricyclic regioisomers, the reaction of 1,2,4,5-tetrakis(bromomethyl)benzene with tosylated diethylenetriamine affords selectively a single product which has been assigned structure 4,7,10,15,18,21-hexakis(4-methylbenzenesulfonyl)-4,7,10,15,18,21-hexa- azatricyclo[11.9.1.12,12]tetracosa-1(23),2(24),12-triene with the aid of X-ray crystal analysis.

Keywords: Crown compounds; Azacrown compounds; Amines; Cyclisations; Macrocycles; N-Ligands; X-Ray diffraction.