Alzahrani, Abdullah, Mirallai, Styliana I., Chalmers, Benjamin A., McArdle, Patrick and 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, 22, pp. 4108-4116. ISSN (print) 1477-0520
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 addition of acrylamide and methacrylamide onto in situ generated or freshly isolated methylene Schiff base (iminium) salts. X-ray crystal structure of the hydrated iminium salt, 1-(hydroxymethyl)azocan-1-ium chloride and monomer.HCl salt, (N-[(azocan-1-yl)methyl]prop-2-enamide hydrochloride) is described.
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