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Issue 22, 2018
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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

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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 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·HCl salt (N-[(azocan-1-yl)methyl]prop-2-enamide hydrochloride) is described.

Graphical abstract: Synthesis of N-[(dialkylamino)methyl]acrylamides and N-[(dialkylamino)methyl]methacrylamides from Schiff base salts: useful building blocks for smart polymers

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Article information


Submitted
05 Apr 2018
Accepted
09 May 2018
First published
09 May 2018

This article is Open Access

Org. Biomol. Chem., 2018,16, 4108-4116
Article type
Paper

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

A. Alzahrani, S. I. Mirallai, B. A. Chalmers, P. McArdle and F. Aldabbagh, Org. Biomol. Chem., 2018, 16, 4108 DOI: 10.1039/C8OB00811F

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