Synlett 2014; 25(11): 1534-1538
DOI: 10.1055/s-0033-1341248
cluster
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Pyridine- and 2-Oxazoline-Functionalized Vinyl Polymers by Alane-Based Frustrated Lewis Pairs

Jianghua He
a  Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523-1872, USA   Fax: +1(970)4911801   Email: eugene.chen@colostate.edu
,
Yuetao Zhang
a  Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523-1872, USA   Fax: +1(970)4911801   Email: eugene.chen@colostate.edu
b  State Key Laboratory of Supramolecular Structure and Materials, College of Chemistry, Jilin University, Changchun 130012, P. R. of China
,
Eugene Y.-X. Chen*
a  Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523-1872, USA   Fax: +1(970)4911801   Email: eugene.chen@colostate.edu
› Author Affiliations
Further Information

Publication History

Received: 16 February 2014

Accepted after revision: 04 April 2014

Publication Date:
28 April 2014 (online)


Abstract

Reported herein is the first example of polymerization of polar vinyl monomers bearing the C=C–C=N functionality by Frustrated Lewis pairs (FLPs). In particular, FLPs based on Al(C6F5)3 and N-heterocyclic carbenes rapidly convert 2-vinyl pyridine and 2-isopropenyl-2-oxazoline into medium to high molecular weight, N-functionalized vinyl polymers. Activated monomer-alane adduct 1 and initiated zwitterionic intermediate 2 have been isolated and structurally characterized, providing strong evidence for the proposed bimolecular, activated monomer polymerization mechanism.

Supporting Information

 
  • References and Notes


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