(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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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.

Item ID: 13415
Item Type: Article (Refereed Research - C1)
Keywords: chiral column; condensation; X-ray crystallography
ISSN: 1362-511X
Date Deposited: 02 Nov 2012 04:02
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%
Citation Count from Web of Science Web of Science 59
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