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 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, ISSN (print) 1477-0520 (Epub Ahead of Print)

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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.

Item Type: Article
Research Area: Chemistry
Faculty, School or Research Centre: Faculty of Science, Engineering and Computing (until 2017) > School of Pharmacy and Chemistry
Related URLs:
Depositing User: Fawaz Al-Dabbagh
Date Deposited: 31 May 2018 13:14
Last Modified: 31 May 2018 13:14
DOI: https://doi.org/10.1039/C8OB00811F
URI: http://eprints.kingston.ac.uk/id/eprint/41156

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