1,3-Dipolar and Diels-Alder cycloaddition reactions on polyester backbones possessing internal electron-deficient alkyne moieties


Cetin M., ESEN C., DAGLAR O., LULEBURGAZ S. , Hızal G. , DURMAZ H. , ...More

POLYMER CHEMISTRY, vol.7, no.46, pp.7094-7100, 2016 (Journal Indexed in SCI) identifier identifier

  • Publication Type: Article / Article
  • Volume: 7 Issue: 46
  • Publication Date: 2016
  • Doi Number: 10.1039/c6py01827k
  • Title of Journal : POLYMER CHEMISTRY
  • Page Numbers: pp.7094-7100

Abstract

In this study we prepared a series of polyesters containing electron deficient internal alkyne units derived from acetylene dicarboxylic acid in the main backbone. Next, one of the polyesters was employed as a polymeric platform in copper free cycloaddition reactions like, Huisgen type 1,3-dipolar and Diels-Alder cycloaddition reactions in the presence of various dipoles and dienes, respectively. The 1,3-dipolar cycloaddition reactions were performed at mild temperatures (rt and 40 degrees C) in 1,4-dioxane for 16 h and had moderately high efficiencies (80-100%). However, the Diels-Alder cycloaddition reactions were carried out at higher temperatures (60 to 120 degrees C) in 1,4-dioxane for 16 h with reasonable efficiencies (45-97%). Moreover, the polyester was successfully used in one-pot 1,3-dipolar, sequential 1,3-dipolar/Diels-Alder, and sequential 1,3-dipolar cycloaddition/retro-Diels-Alder reactions.