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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
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.
Keyword(s): dimethyl(methylene)ammonium iodide; aqueous-solution; mannich; sensitivity; derivatives; aminals; acid
Publication Date:
Type: Journal article
Peer-Reviewed: Unknown
Institution: NUI Galway
Publisher(s): Royal Society of Chemistry (RSC)
First Indexed: 2019-03-23 06:50:14 Last Updated: 2019-03-23 06:50:14