Templated versus non-templated synthesis of benzo-21-crown-7 and the influence of substituents on its complexing properties

Two procedures for the synthesis of benzo-21-crown-7 have been explored. The [1+1] macrocyclization with KBF(4) as the template was found to be more efficient than the intramolecular macrocyclization without template. Pseudorotaxanes form with secondary ammonium ions bearing at least one alkyl chain...

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Autores principales: Jiang, Wei, Schalley, Christoph A
Formato: Texto
Lenguaje:English
Publicado: Beilstein-Institut 2010
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2869786/
https://www.ncbi.nlm.nih.gov/pubmed/20485596
http://dx.doi.org/10.3762/bjoc.6.14
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author Jiang, Wei
Schalley, Christoph A
author_facet Jiang, Wei
Schalley, Christoph A
author_sort Jiang, Wei
collection PubMed
description Two procedures for the synthesis of benzo-21-crown-7 have been explored. The [1+1] macrocyclization with KBF(4) as the template was found to be more efficient than the intramolecular macrocyclization without template. Pseudorotaxanes form with secondary ammonium ions bearing at least one alkyl chain narrow enough to slip into the crown ether. Substitution on benzo-21-crown-7 or on the secondary ammonium axle alters the binding affinity and binding mode. Compared to dibenzo-24-crown-8, the complexing properties of benzo-21-crown-7 turn out to be more susceptible to modifications at the crown periphery.
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spelling pubmed-28697862010-05-18 Templated versus non-templated synthesis of benzo-21-crown-7 and the influence of substituents on its complexing properties Jiang, Wei Schalley, Christoph A Beilstein J Org Chem Full Research Paper Two procedures for the synthesis of benzo-21-crown-7 have been explored. The [1+1] macrocyclization with KBF(4) as the template was found to be more efficient than the intramolecular macrocyclization without template. Pseudorotaxanes form with secondary ammonium ions bearing at least one alkyl chain narrow enough to slip into the crown ether. Substitution on benzo-21-crown-7 or on the secondary ammonium axle alters the binding affinity and binding mode. Compared to dibenzo-24-crown-8, the complexing properties of benzo-21-crown-7 turn out to be more susceptible to modifications at the crown periphery. Beilstein-Institut 2010-02-11 /pmc/articles/PMC2869786/ /pubmed/20485596 http://dx.doi.org/10.3762/bjoc.6.14 Text en Copyright © 2010, Jiang and Schalley https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Jiang, Wei
Schalley, Christoph A
Templated versus non-templated synthesis of benzo-21-crown-7 and the influence of substituents on its complexing properties
title Templated versus non-templated synthesis of benzo-21-crown-7 and the influence of substituents on its complexing properties
title_full Templated versus non-templated synthesis of benzo-21-crown-7 and the influence of substituents on its complexing properties
title_fullStr Templated versus non-templated synthesis of benzo-21-crown-7 and the influence of substituents on its complexing properties
title_full_unstemmed Templated versus non-templated synthesis of benzo-21-crown-7 and the influence of substituents on its complexing properties
title_short Templated versus non-templated synthesis of benzo-21-crown-7 and the influence of substituents on its complexing properties
title_sort templated versus non-templated synthesis of benzo-21-crown-7 and the influence of substituents on its complexing properties
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2869786/
https://www.ncbi.nlm.nih.gov/pubmed/20485596
http://dx.doi.org/10.3762/bjoc.6.14
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AT schalleychristopha templatedversusnontemplatedsynthesisofbenzo21crown7andtheinfluenceofsubstituentsonitscomplexingproperties

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