Synthesis of Symmetric Dinitro-Functionalised Troger's Base Analogues

The synthesis of six new examples of 2,8-dinitro-substituted Troger's base analogues are reported, together with the first examples of 1,7-, 3,9- and 4,10-dinitro Troger's base analogues and the first example of a tetranitro Troger's base compound. Several of these dinitro compounds lack substituents at the 2- and 8-positions and therefore provide further examples of Troger's base analogues derived from anilines lacking a para substituent. (C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)