Extremely rapid postfunctionalization of maleate and fumarate main chain polyesters in the presence of TBD

Ozgun Daglar; Buse Ozcan; Ufuk Saim Gunay; Gurkan Hizal; Umit Tunca; Hakan Durmaz

doi:10.1016/j.polymer.2019.121844

Extremely rapid postfunctionalization of maleate and fumarate main chain polyesters in the presence of TBD

Ozgun Daglar, Buse Ozcan, Ufuk Saim Gunay, Gurkan Hizal, Umit Tunca, Hakan Durmaz^*

^*Corresponding author for this work

Department of Chemistry

Istanbul Technical University

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

16 Citations (Scopus)

Abstract

Unsaturated polyester (UP) scaffold, poly (butylene maleate) (P1), possessing an electron-deficient double bond in the main chain was prepared and utilized as a precursor for thiol- and aza-Michael addition reactions. From a detailed catalyst search (amidine and guanidine bases), 1,5,7-triazabicyclo [4.4.0]dec-5-ene (TBD) proved to be the most efficient catalyst for thiol-Michael addition reactions since pendant thioether functional polyesters were achieved quantitatively within 1 min. Furthermore, P1 was allowed to react with primary and secondary amines through aza-Michael addition reactions, followed by thiol-Michael addition reaction thus affording the synthesis of pendant amine and thioether functional polyesters.

Original language	English
Article number	121844
Journal	Polymer
Volume	182
DOIs	https://doi.org/10.1016/j.polymer.2019.121844
Publication status	Published - 7 Nov 2019

Bibliographical note

Publisher Copyright:
© 2019 Elsevier Ltd

Funding

This work was supported by the Research Fund of Istanbul Technical University (Project Number: TDK-2018-41700). This work was supported by the Research Fund of Istanbul Technical University (Project Number: TDK-2018-41700 ).

Funders	Funder number
Research Fund of
Istanbul Teknik Üniversitesi	TDK-2018-41700

Keywords

Aza-Michael
Organocatalyst
Postfunctionalization
Thiol-Michael
Unsaturated polyester

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10.1016/j.polymer.2019.121844

Cite this

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title = "Extremely rapid postfunctionalization of maleate and fumarate main chain polyesters in the presence of TBD",

abstract = "Unsaturated polyester (UP) scaffold, poly (butylene maleate) (P1), possessing an electron-deficient double bond in the main chain was prepared and utilized as a precursor for thiol- and aza-Michael addition reactions. From a detailed catalyst search (amidine and guanidine bases), 1,5,7-triazabicyclo [4.4.0]dec-5-ene (TBD) proved to be the most efficient catalyst for thiol-Michael addition reactions since pendant thioether functional polyesters were achieved quantitatively within 1 min. Furthermore, P1 was allowed to react with primary and secondary amines through aza-Michael addition reactions, followed by thiol-Michael addition reaction thus affording the synthesis of pendant amine and thioether functional polyesters.",

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author = "Ozgun Daglar and Buse Ozcan and Gunay, \{Ufuk Saim\} and Gurkan Hizal and Umit Tunca and Hakan Durmaz",

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AU - Daglar, Ozgun

AU - Ozcan, Buse

AU - Gunay, Ufuk Saim

AU - Hizal, Gurkan

AU - Tunca, Umit

AU - Durmaz, Hakan

PY - 2019/11/7

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N2 - Unsaturated polyester (UP) scaffold, poly (butylene maleate) (P1), possessing an electron-deficient double bond in the main chain was prepared and utilized as a precursor for thiol- and aza-Michael addition reactions. From a detailed catalyst search (amidine and guanidine bases), 1,5,7-triazabicyclo [4.4.0]dec-5-ene (TBD) proved to be the most efficient catalyst for thiol-Michael addition reactions since pendant thioether functional polyesters were achieved quantitatively within 1 min. Furthermore, P1 was allowed to react with primary and secondary amines through aza-Michael addition reactions, followed by thiol-Michael addition reaction thus affording the synthesis of pendant amine and thioether functional polyesters.

AB - Unsaturated polyester (UP) scaffold, poly (butylene maleate) (P1), possessing an electron-deficient double bond in the main chain was prepared and utilized as a precursor for thiol- and aza-Michael addition reactions. From a detailed catalyst search (amidine and guanidine bases), 1,5,7-triazabicyclo [4.4.0]dec-5-ene (TBD) proved to be the most efficient catalyst for thiol-Michael addition reactions since pendant thioether functional polyesters were achieved quantitatively within 1 min. Furthermore, P1 was allowed to react with primary and secondary amines through aza-Michael addition reactions, followed by thiol-Michael addition reaction thus affording the synthesis of pendant amine and thioether functional polyesters.

KW - Aza-Michael

KW - Organocatalyst

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KW - Thiol-Michael

KW - Unsaturated polyester

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Extremely rapid postfunctionalization of maleate and fumarate main chain polyesters in the presence of TBD

Abstract

Bibliographical note

Funding

Keywords

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