Anionic oligomerization of acrylamide by alkali metal methoxides

Shmuel Dabi*, Albert Zilkha

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

3 Scopus citations

Abstract

The anionic oligomerization of acrylamide by methanolic alkali metal methoxides was studied in methanol and in aprotic solvents. Oligomer yield increased with increasing initiator concentration, the dielectric constant of the solvent, the electropositivity of the alkali metal and with decrease in methanol concentration. Initiation occurred by addition of methoxide to the double bond. Simultaneous monitoring of the reactants and products showed that β-methoxypropionamide, first formed in up to 70% yield, undergoes a base-catalysed reversible reaction generating acrylamide which participates in propagation. Acid hydrolysis of the oligomers showed that propagation had proceeded through 1.2-addition (30-50%) leading to an acrylamide structure. and 1.4-addition (50-70%) leading to a β-alanine structure in the polymers.

Original languageEnglish
Pages (from-to)545-552
Number of pages8
JournalEuropean Polymer Journal
Volume13
Issue number7
DOIs
StatePublished - 1977

Fingerprint

Dive into the research topics of 'Anionic oligomerization of acrylamide by alkali metal methoxides'. Together they form a unique fingerprint.

Cite this