Macrocyclic cyclo[n]malonates - Synthetic aspects and observation of columnar arrangements by X-ray crystallography
Chronakis N, Brandmüller T, Kovács C, Reuther U, Donaubauer W, Hampel F, Fischer F, Diederich F, Hirsch A (2006)
Publication Type: Journal article, Original article
Publication year: 2006
Journal
Original Authors: Chronakis N., Brandmüller T., Kovacs C., Reuther U., Donaubauer W., Hampel F., Fischer F., Diederich F., Hirsch A.
Publisher: Wiley-VCH Verlag
Pages Range: 2296-2308
Journal Issue: 10
Abstract
A variety of achiral and chiral macrocyclic oligomalonates were synthesised in a one-step procedure through condensation of malonyl dichloride with α,ω-diols. We have investigated the applicability of this method by varying the length and type of the spacers in the diol. Product distribution analysis revealed that the preferential formation of monomeric, dimeric, or trimeric macrocyclic malonates can be controlled by choosing diols with specific spacers connecting the hydroxy groups. Of special interest are the macrocyclic bismalonates, as they show pronounced crystallisability and arrange into columnar motifs in the solid state. They feature distinctive dihedral angles: all ester moieties adopt anti conformations whereas the planes of the carboxy moieties of each malonate residue arrange in an approximately orthogonal fashion. The latter geometry is enforced by the macrocyclic structures, as revealed by a conformational search in the Cambridge Structural Database. The X-ray diffraction data show that C=O⋯H-C, and C-O⋯H-C hydrogen bonds stabilise the columnar arrangement of the dimeric rings with formation of tubular assemblies. © Wiley-VCH Verlag GmbH & Co. KGaA, 2006.
Authors with CRIS profile
Wolfgang Donaubauer
Lehrstuhl für Organische Chemie I
Frank Hampel
Lehrstuhl für Organische Chemie I
Andreas Hirsch
Lehrstuhl für Organische Chemie II
Involved external institutions
Switzerland (CH)How to cite
APA:
Chronakis, N., Brandmüller, T., Kovács, C., Reuther, U., Donaubauer, W., Hampel, F.,... Hirsch, A. (2006). Macrocyclic cyclo[n]malonates - Synthetic aspects and observation of columnar arrangements by X-ray crystallography. European Journal of Organic Chemistry, 10, 2296-2308. https://doi.org/10.1002/ejoc.200500921
MLA:
Chronakis, Nikos, et al. "Macrocyclic cyclo[n]malonates - Synthetic aspects and observation of columnar arrangements by X-ray crystallography." European Journal of Organic Chemistry 10 (2006): 2296-2308.
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