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

Christina Wappl; Viktor Schallert; Christian Slugovc; Astrid-Caroline Knall; Stefan Spirk

doi:10.3390/molecules26051358

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

Christina Wappl, Viktor Schallert, Christian Slugovc, Astrid-Caroline Knall^*, Stefan Spirk^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

Abstract

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

Original language	English
Article number	1358
Journal	Molecules
Volume	26
Issue number	5
DOIs	https://doi.org/10.3390/molecules26051358
Publication status	Published - 4 Mar 2021

Keywords

Cellulose
Cellulose ester
Click chemistry
Copper-free
Norbornene cellulose
iEDDA

ASJC Scopus subject areas

Analytical Chemistry
Chemistry (miscellaneous)
Molecular Medicine
Pharmaceutical Science
Drug Discovery
Physical and Theoretical Chemistry
Organic Chemistry

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

abstract = "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",

keywords = "Cellulose, Cellulose ester, Click chemistry, Copper-free, Norbornene cellulose, iEDDA",

author = "Christina Wappl and Viktor Schallert and Christian Slugovc and Astrid-Caroline Knall and Stefan Spirk",

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T1 - Highly Norbornylated Cellulose and Its “Click” Modification by an Inverse-Electron Demand Diels–Alder (iEDDA) Reaction

AU - Wappl, Christina

AU - Schallert, Viktor

AU - Slugovc, Christian

AU - Knall, Astrid-Caroline

AU - Spirk, Stefan

PY - 2021/3/4

Y1 - 2021/3/4

N2 - 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

AB - 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

KW - Cellulose

KW - Cellulose ester

KW - Click chemistry

KW - Copper-free

KW - Norbornene cellulose

KW - iEDDA

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U2 - 10.3390/molecules26051358

DO - 10.3390/molecules26051358

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

Abstract

Keywords

ASJC Scopus subject areas

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