(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, and Junk, Peter C. (2001) (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. Tetrahedron: Asymmetry, 12 (1). pp. 127-133.
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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.
|Item Type:||Article (Refereed Research - C1)|
|Keywords:||chiral column; condensation; X-ray crystallography|
|FoR Codes:||03 CHEMICAL SCIENCES > 0305 Organic Chemistry > 030503 Organic Chemical Synthesis @ 100%|
|SEO Codes:||97 EXPANDING KNOWLEDGE > 970103 Expanding Knowledge in the Chemical Sciences @ 100%|
|Deposited On:||02 Nov 2012 14:02|
|Last Modified:||02 Nov 2012 18:02|
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