TY - JOUR
T1 - Anionic oligomerization of acrylamide by alkali metal methoxides
AU - Dabi, Shmuel
AU - Zilkha, Albert
PY - 1977
Y1 - 1977
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=49449127106&partnerID=8YFLogxK
U2 - 10.1016/0014-3057(77)90181-1
DO - 10.1016/0014-3057(77)90181-1
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AN - SCOPUS:49449127106
SN - 0014-3057
VL - 13
SP - 545
EP - 552
JO - European Polymer Journal
JF - European Polymer Journal
IS - 7
ER -