Diels-Alder reactions as an efficient route to high purity cyclic polymers

Mathias Glassner; James P Blinco; Christopher Barner-Kowollik

doi:10.1002/marc.201100094

Diels-Alder reactions as an efficient route to high purity cyclic polymers

Macromol Rapid Commun. 2011 May 18;32(9-10):724-8. doi: 10.1002/marc.201100094. Epub 2011 Mar 17.

Authors

Mathias Glassner¹, James P Blinco, Christopher Barner-Kowollik

Affiliation

¹ Preparative Macromolecular Chemistry, Institut für Technische Chemie und Polymerchemie, Karlsruhe Institute of Technology, Engesserstrasse 18, Karlsruhe, Germany.

PMID: 21544892
DOI: 10.1002/marc.201100094

Abstract

A simple and efficient route for the synthesis of cyclic polymer systems is presented. Linear furan protected α-maleimide-ω-cyclopentadienyl functionalized precursors (poly(methyl methacrylate) and poly(tert-butyl acrylate)) were synthesized via atom transfer radical polymerization (ATRP) and subsequent substitution of the bromine end-group with cyclopentadiene. Upon heating at high dilution, deprotection of the dieneophile occurs followed by an intramolecular Diels-Alder reaction yielding a high purity cyclic product.

Publication types

Evaluation Study
Research Support, Non-U.S. Gov't

MeSH terms

Acrylates / chemistry*
Chemistry, Organic / methods*
Molecular Structure
Polymerization
Polymers / chemical synthesis*
Polymers / chemistry
Polymethyl Methacrylate / chemistry*

Substances

Acrylates
Polymers
poly(tert-butyl acrylate)
Polymethyl Methacrylate