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Synthesis of n-[(dialkylamino)methyl)]acrylamides and n-[(dialkylamino)methyl]methacrylamides from schiff base salts: useful building blocks for smart polymers

Alzahrani, Abdullah
; 
Mirallai, Styliana I
; 
Chalmers, Benjamin A
; 
McArdle, Patrick
; 
Aldabbagh, Fawaz
Identifiers
http://hdl.handle.net/10379/10235
 https://doi.org/10.13025/24854
Publication Date
2018-01-01
Keywords
dimethyl(methylene)ammonium iodide, aqueous-solution, mannich, sensitivity, derivatives, aminals, acid
Type
Article
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Citation
Alzahrani, Abdullah; Mirallai, Styliana I; Chalmers, Benjamin A; McArdle, Patrick; Aldabbagh, Fawaz (2018). Synthesis of n-[(dialkylamino)methyl)]acrylamides and n-[(dialkylamino)methyl]methacrylamides from schiff base salts: useful building blocks for smart polymers. Organic & Biomolecular Chemistry 16 (22), 4108-4116
Abstract
The traditional thermal Mannich reaction is unsuitable for preparing polymerizable N-methylene amino substituted acrylamides and methacrylamides. Herein we provide a facile multi-gram high yield synthesis of these monomeric precursors to stimuli-responsive polymers by the addition of acrylamides and methacrylamides onto in situ generated or freshly isolated methylene Schiff base (iminium) salts. The X-ray crystal structure of the hydrated iminium salt, 1-(hydroxymethyl)azocan-1-ium chloride and monomer center dot HCl salt (N-[(azocan-1-yl)methyl]prop-2-enamide hydrochloride) is described.
Funder
Publisher
Royal Society of Chemistry (RSC)
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Attribution-NonCommercial-NoDerivs 3.0 Ireland
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Externally hosted open access publications with University of Galway authors (2)