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2‐[(1‐Imidazolyl)formyloxy]ethyl Methacrylate as Selective Methacryloylating Agent: Kinetics of Reaction with Model Alcohols and Amines
Author(s) -
Ranucci Elisabetta,
Grigolini Michela,
Ferruti Paolo
Publication year - 2003
Publication title -
macromolecular bioscience
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.924
H-Index - 105
eISSN - 1616-5195
pISSN - 1616-5187
DOI - 10.1002/mabi.200350036
Subject(s) - triethylamine , chemistry , imidazole , catalysis , methacrylate , selectivity , monomer , coupling reaction , polymer chemistry , kinetics , organic chemistry , medicinal chemistry , polymer , physics , quantum mechanics
The kinetics of the coupling reactions of 2‐[(1‐imidazolyl)formyloxy]ethyl methacrylate (HEMA‐Im) with model primary and secondary alcohols and amines have been investigated both in the absence and in the presence of imidazole and triethylamine as catalysts. In the absence of added catalysts, alcohols either reacted very sluggishly or did not react at all with HEMA‐Im, but amines reacted completely in relatively short times. In the presence of catalysts, both primary and secondary alcohols underwent coupling reactions with HEMA‐Im, the former about ten times faster than the latter. Imidazole was a more effective catalyst than triethylamine. HEMA‐Im's ability to discriminate between amino and hydroxyl groups was tested with 4‐amino‐1‐butanol: the 1 H NMR analysis of the reaction product confirmed 100% selectivity towards the amino group. It was therefore concluded that HEMA‐Im is a highly selective methacryloylating agent, with a synthetic potential for preparing multifunctional monomers and polymers.Reaction curves for HEMA‐Im with EtOH and Pr i OH at 37 °C in the presence of imidazole (HEM5 and HEM6) and triethylamine (HEM7 and HEM8).