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^*

^*Bu çalışma için yazışmadan sorumlu yazar

Kimya Bölümü

Istanbul Technical University

Araştırma çıktısı: Dergi yayını › Makale › Hakem

16 Atıf (Scopus)

Özet

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.

Orijinal dil	İngilizce
Makale numarası	121844
Dergi	Polymer
Hacim	182
DOI'lar	https://doi.org/10.1016/j.polymer.2019.121844
Yayın durumu	Yayınlandı - 7 Kas 2019

Bibliyografik not

Publisher Copyright:
© 2019 Elsevier Ltd

Finansman

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 ).

Finansörler	Finansör numarası
Research Fund of
Istanbul Teknik Üniversitesi	TDK-2018-41700

Belgeye Erişim

10.1016/j.polymer.2019.121844

Diğer Dosyalar ve Linkler

Link to publication in Scopus

Alıntı Yap

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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.",

keywords = "Aza-Michael, Organocatalyst, Postfunctionalization, Thiol-Michael, Unsaturated polyester",

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

note = "Publisher Copyright: {\textcopyright} 2019 Elsevier Ltd",

year = "2019",

month = nov,

day = "7",

doi = "10.1016/j.polymer.2019.121844",

language = "English",

volume = "182",

journal = "Polymer",

issn = "0032-3861",

}

TY - JOUR

T1 - Extremely rapid postfunctionalization of maleate and fumarate main chain polyesters in the presence of TBD

AU - Daglar, Ozgun

AU - Ozcan, Buse

AU - Gunay, Ufuk Saim

AU - Hizal, Gurkan

AU - Tunca, Umit

AU - Durmaz, Hakan

PY - 2019/11/7

Y1 - 2019/11/7

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

KW - Postfunctionalization

KW - Thiol-Michael

KW - Unsaturated polyester

UR - https://www.scopus.com/pages/publications/85072702861

U2 - 10.1016/j.polymer.2019.121844

DO - 10.1016/j.polymer.2019.121844

M3 - Article

AN - SCOPUS:85072702861

SN - 0032-3861

VL - 182

JO - Polymer

JF - Polymer

M1 - 121844

ER -

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

Özet

Bibliyografik not

Finansman

Belgeye Erişim

Diğer Dosyalar ve Linkler

Parmak izi

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