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

P.H. Findlay, D.C. Sherrington

Research output: Contribution to journalArticle

8 Citations (Scopus)

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.
LanguageEnglish
Pages5970-5972
Number of pages3
JournalMacromolecules
Volume32
Issue number18
DOIs
Publication statusPublished - 7 Sep 1999

Fingerprint

Transesterification
Ethanol
Monomers
Dextran
Chelation
Methacrylates
Ligands
Dextrans
Polymers
Metals
glycidyl methacrylate

Keywords

  • transesterification
  • glycidyl methacrylate
  • 2-{[-2(dimethylamino)ethyl]methylamino}ethanol

Cite this

@article{a1a505cb37ec4a46a68b3c5c11f5712e,
title = "The unexpected transesterification between glycidyl methacrylate and 2-{[-2(dimethylamino)ethyl] methylamino}ethanol",
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.",
keywords = "transesterification, glycidyl methacrylate, 2-{[-2(dimethylamino)ethyl]methylamino}ethanol",
author = "P.H. Findlay and D.C. Sherrington",
year = "1999",
month = "9",
day = "7",
doi = "10.1021/ma990590p",
language = "English",
volume = "32",
pages = "5970--5972",
journal = "Macromolecules",
issn = "0024-9297",
publisher = "American Chemical Society",
number = "18",

}

The unexpected transesterification between glycidyl methacrylate and 2-{[-2(dimethylamino)ethyl] methylamino}ethanol. / Findlay, P.H.; Sherrington, D.C.

In: Macromolecules, Vol. 32, No. 18, 07.09.1999, p. 5970-5972.

Research output: Contribution to journalArticle

TY - JOUR

T1 - The unexpected transesterification between glycidyl methacrylate and 2-{[-2(dimethylamino)ethyl] methylamino}ethanol

AU - Findlay, P.H.

AU - Sherrington, D.C.

PY - 1999/9/7

Y1 - 1999/9/7

N2 - 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.

AB - 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.

KW - transesterification

KW - glycidyl methacrylate

KW - 2-{[-2(dimethylamino)ethyl]methylamino}ethanol

U2 - 10.1021/ma990590p

DO - 10.1021/ma990590p

M3 - Article

VL - 32

SP - 5970

EP - 5972

JO - Macromolecules

T2 - Macromolecules

JF - Macromolecules

SN - 0024-9297

IS - 18

ER -