Collect. Czech. Chem. Commun. 2006, 71, 1278-1302

A New Bis-Tröger's Base: Synthesis, Spectroscopy, Crystal Structure and Isomerization

Martin Valíka, Pavel Matějkaa, Eberhardt Herdtweckb, Vladimír Krála and Bohumil Dolenskya,*

a Department of Analytical Chemistry, Institute of Chemical Technology, Prague, Technická 5, 166 28 Prague 6, Czech Republic
b Department of Inorganic Chemistry, Technische Universität München, Lichtenbergstraße 4, D-85747 Garching, Germany


A new bis-Tröger's base was prepared from a tetraamine precursor as a mixture of two diastereoisomers. One of the isomers has a chair-like geometry, and the other possesses a boat-like geometry, embodying molecular tweezers. A one-pot preparation of bis-TB isomers and their interconversion under acid conditions was also studied. Structures of both isomers were confirmed by single-crystal X-ray diffraction. Extensive spectroscopic data, including 1H and 13C NMR, IR and Raman spectra of the isomers, are given.

Keywords: Molecular tweezers; Tröger's bases; Chiral receptors; Isomerization; IR/Raman spectroscopy; NMR spectroscopy; X-Ray diffraction.

References: 39 live references.