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The unexpected transesterification between glycidyl methacrylate and 2-{[-2(dimethylamino)ethyl]methylamino}ethanol

Findlay, P.H. and Sherrington, D.C. (1999) The unexpected transesterification between glycidyl methacrylate and 2-{[-2(dimethylamino)ethyl]methylamino}ethanol. Macromolecules, 32 (18). pp. 5970-5972. ISSN 0024-9297

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Abstract

In the course of some recent work involving novel metal chelating polymers,1 we identified monomer 1 as an attractive target monomer in view of its likely hydrophilic character, the presence of a substantial flexible linkage between the diamino ligand functionality and the methacrylate residue, and the likely ease of synthesis from commercially available glycidyl methacrylate (GMA) and 2-{[2(dimethylamino)ethyl]methylamino}ethanol (DAEMAE) via Scheme 1. While evaluating likely reaction conditions, we had occasion to perform one reaction without NaH and to our surprise were able to synthesize a product similar to 1 but clearly lacking the glycidyl derived spacer group in 1. Indeed, the analytical data suggested the product to be 2 (Figure 1), presumably arising from a transesterification reaction involving GMA and DAEMAE. Interestingly, we noted a similar reaction to this, between GMA and dextran, reported recently in this journal.2 This paper reports our efforts to understand the basis of this reaction and to probe its generality.

Item type: Article
ID code: 17520
Keywords: transesterification, glycidyl methacrylate, 2-{[-2(dimethylamino)ethyl]methylamino}ethanol, Chemistry, Materials Chemistry, Organic Chemistry, Polymers and Plastics, Inorganic Chemistry
Subjects: Science > Chemistry
Department: Faculty of Science > Pure and Applied Chemistry
Unknown Department
Related URLs:
    Depositing user: Strathprints Administrator
    Date Deposited: 22 Apr 2010 14:22
    Last modified: 05 Sep 2014 01:06
    URI: http://strathprints.strath.ac.uk/id/eprint/17520

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