(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.

[img] PDF (Published Version) - Published Version
Restricted to Repository staff only

View at Publisher Website: http://dx.doi.org/10.1016/S0957-4166(00)...
 
87
4


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 (Research - C1)
ISSN: 1362-511X
Keywords: chiral column; condensation; X-ray crystallography
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%
Downloads: Total: 4
More Statistics

Actions (Repository Staff Only)

Item Control Page Item Control Page