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


Daglar O., Tunca Ü. , Tunca Ü. , Hızal G. , Tunca Ü. , Durmaz H.

POLYMER, vol.182, 2019 (Journal Indexed in SCI) identifier identifier

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.