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Updated: Aug 23, 2026

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
Design and synthesis of a C2-symmetric self-complementary hydrogen-bonding cleft molecule based on the
Sigitas Stoncius1, Eugenius Butkus, Albinas Zilinskas
1Department of Organic Chemistry, Vilnius University, Naugarduko 24, LT03225 Vilnius, Lithuania.
Abstract:
The synthesis of a C2-symmetric cleft molecule 2 based on the fused framework between bicyclo[3.3.1]nonane and 4-oxo-5-azaindole, incorporating a self-complementary hydrogen-bonding motif, in both racemic and enantiomerically pure forms is reported. This cleft molecule is reminiscent of analogues of Tröger's base though with different cleft dimensions and tilt angles. The framework of 2 provides a building block for the construction of self-assembled hydrogen-bonded supramolecular structures. The solid-state structure of 2 is highly influenced by the limited solubility of (+/-)-2 and (-)-2. The solvents interact with the potential hydrogen-bonding motifs of (+/-)-2 and (-)-2, forming different three-dimensional structures as revealed by X-ray diffraction analysis. In the solid state (+/-)-(2)2 x 5DMF forms hydrogen-bonded pleated band structures that build up three-dimensional pens between adjacent bands in which two molecules of DMF are trapped. In contrast, the aggregate obtained from (-)-2, (-)-2 x 2AcOH, showed infinite bands of complex constitution.
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