(3+3)-cyclocondensation of the enantiopure and racemic forms of trans-1,2-diaminocyclohexane with terephthaldehyde: formation of diastereomeric molecular triangles and their stereoselective solid-state stacking into microporous chiral columns

Chadim, Martin;Buděšı́nský, Miloš;Hodačová, Jana;Závada, Jiřı́;Junk, Peter C.

Abstract

The non-templated reaction of both the homochiral as well as the racemic form of trans-1,2-diaminocyclohexane with terephthaldehyde affords (3+3)-cyclocondensed molecular triangles in practically quantitative yields. The configuration of the diastereomeric products resulting in the individual reactions has been determined by ¹H and ¹³C NMR spectroscopy. Unambiguous proof has been obtained by X-ray crystal structure analysis of both alternative diastereomers, revealing also a stereoselective stacking of the triangles into microporous chiral columns.

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1362-511X

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Elsevier

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10.1016/S0957-4166(00)00494-8