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Molecules 2016, 21(2), 171; doi:10.3390/molecules21020171

Synthesis and Characterization of Macrocyclic Polyether N,N′-Diallyl-7,16-diaza-1,4,10,13-tetraoxa-dibenzo-18-crown-6

1
Freiburg Materials Research Center, Stefan-Meier-Straße 21, 79104 Freiburg, Germany
2
Chair of Forest Biomaterials, University of Freiburg, Werthmanstr. 6, 79085 Freiburg, Germany
*
Author to whom correspondence should be addressed.
Academic Editor: Derek J. McPhee
Received: 14 December 2015 / Revised: 25 January 2016 / Accepted: 27 January 2016 / Published: 29 January 2016
(This article belongs to the Section Organic Synthesis)
View Full-Text   |   Download PDF [1677 KB, uploaded 29 January 2016]   |  

Abstract

In this study an efficient and direct production procedure for a macrocyclic polyether N,N′-diallyl-7,16-diaza-1,4,10,13-tetraoxa-dibenzo-18-crown-6 from the reaction of catechol and N,N-bis(2-chloroethyl)prop-2-en-1-amine in n-butanol in the presence of a strong base is reported. The synthesis involves a two-step addition of sodium hydroxide to enhance the cyclization process, and at the end of the reaction, the reaction mixture is neutralized and the solvent replaced with water in-situ through distillation to afford a relatively pure precipitate that is easily recrystallized from acetone. The yield of the macrocycle was 36%–45% and could be scaled-up to one-mole quantities. The structure and purity of this compound was verified on the basis of elemental analysis, IR, UV-Vis, 1H-, 13C-NMR, 2D-NMR, mass spectroscopy, and thermal analysis. The white crystalline compound has a sharp melting point of 124 °C and a crystallization temperature of 81.4 °C determined by differential scanning calorimetry. Our motivation behind the synthesis of the bibracchial lariat azacrown polyether ligand was to examine its possible applications in ion-selective polymer-supported materials. View Full-Text
Keywords: N-substituted azacrown polyether; 4,16-diaza-18-crown-6; synthesis; lariat azacrown ether; molecular recognition N-substituted azacrown polyether; 4,16-diaza-18-crown-6; synthesis; lariat azacrown ether; molecular recognition
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Toeri, J.; Laborie, M.-P. Synthesis and Characterization of Macrocyclic Polyether N,N′-Diallyl-7,16-diaza-1,4,10,13-tetraoxa-dibenzo-18-crown-6. Molecules 2016, 21, 171.

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