Highly Norbornylated Cellulose and Its “Click” Modification by an Inverse-Electron Demand Diels–Alder (iEDDA) Reaction

A facile, catalyst-free synthesis of a norbornylated cellulosic material (NC) with a high degree of substitution (2.9) is presented by direct reaction of trimethylsilyl cellulose with norbornene acid chloride. The resulting NC is highly soluble in organic solvents and its reactive double bonds were...

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Autores principales: Wappl, Christina, Schallert, Viktor, Slugovc, Christian, Knall, Astrid-Caroline, Spirk, Stefan
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2021
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7961350/
https://www.ncbi.nlm.nih.gov/pubmed/33806278
http://dx.doi.org/10.3390/molecules26051358
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author Wappl, Christina
Schallert, Viktor
Slugovc, Christian
Knall, Astrid-Caroline
Spirk, Stefan
author_facet Wappl, Christina
Schallert, Viktor
Slugovc, Christian
Knall, Astrid-Caroline
Spirk, Stefan
author_sort Wappl, Christina
collection PubMed
description A facile, catalyst-free synthesis of a norbornylated cellulosic material (NC) with a high degree of substitution (2.9) is presented by direct reaction of trimethylsilyl cellulose with norbornene acid chloride. The resulting NC is highly soluble in organic solvents and its reactive double bonds were exploited for the copper-free inverse-electron demand Diels–Alder (iEDDA) “click” reaction with 3,6-di(pyridin-2-yl)-1,2,4,5-tetrazine. Reaction kinetics are comparable to the well-known Huisgen type 1,3-dipolar cycloaddition of azide with alkynes, while avoiding toxic catalysts.
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spelling pubmed-79613502021-03-17 Highly Norbornylated Cellulose and Its “Click” Modification by an Inverse-Electron Demand Diels–Alder (iEDDA) Reaction Wappl, Christina Schallert, Viktor Slugovc, Christian Knall, Astrid-Caroline Spirk, Stefan Molecules Article A facile, catalyst-free synthesis of a norbornylated cellulosic material (NC) with a high degree of substitution (2.9) is presented by direct reaction of trimethylsilyl cellulose with norbornene acid chloride. The resulting NC is highly soluble in organic solvents and its reactive double bonds were exploited for the copper-free inverse-electron demand Diels–Alder (iEDDA) “click” reaction with 3,6-di(pyridin-2-yl)-1,2,4,5-tetrazine. Reaction kinetics are comparable to the well-known Huisgen type 1,3-dipolar cycloaddition of azide with alkynes, while avoiding toxic catalysts. MDPI 2021-03-04 /pmc/articles/PMC7961350/ /pubmed/33806278 http://dx.doi.org/10.3390/molecules26051358 Text en © 2021 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Wappl, Christina
Schallert, Viktor
Slugovc, Christian
Knall, Astrid-Caroline
Spirk, Stefan
Highly Norbornylated Cellulose and Its “Click” Modification by an Inverse-Electron Demand Diels–Alder (iEDDA) Reaction
title Highly Norbornylated Cellulose and Its “Click” Modification by an Inverse-Electron Demand Diels–Alder (iEDDA) Reaction
title_full Highly Norbornylated Cellulose and Its “Click” Modification by an Inverse-Electron Demand Diels–Alder (iEDDA) Reaction
title_fullStr Highly Norbornylated Cellulose and Its “Click” Modification by an Inverse-Electron Demand Diels–Alder (iEDDA) Reaction
title_full_unstemmed Highly Norbornylated Cellulose and Its “Click” Modification by an Inverse-Electron Demand Diels–Alder (iEDDA) Reaction
title_short Highly Norbornylated Cellulose and Its “Click” Modification by an Inverse-Electron Demand Diels–Alder (iEDDA) Reaction
title_sort highly norbornylated cellulose and its “click” modification by an inverse-electron demand diels–alder (iedda) reaction
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7961350/
https://www.ncbi.nlm.nih.gov/pubmed/33806278
http://dx.doi.org/10.3390/molecules26051358
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