Collect. Czech. Chem. Commun. 2007, 72, 392-402

Methodology for Easy Access to Large Sidewall Bis-Tröger's Bases

Martin Havlík, Vladimír Král and Bohumil Dolensky*

Department of Analytical Chemistry, Institute of Chemical Technology, Prague, Technická 5, 166 28 Prague 6, Czech Republic


4,6-Bis(bromomethyl)-N1,N3-bis(tert-butoxycarbonyl)benzene-1,3-diamine is introduced as a general starting compound for the preparation of bis-Tröger's base (bisTB) derivatives in excellent yield in just two steps. The synthetic sequence includes treatment of the above-mentioned protected diamine with an arylamine followed by in situ deprotection and the final bisTB-forming reaction. This sequence allows synthesis of bisTB derivatives, which are not accessible by known procedures. The described approach is a general new method for the preparation of bisTB derivatives from "troegerable" arylamines.

Keywords: Bis-Tröger's bases; Molecular tweezers; Synthetic methodology.

References: 22 live references.