Ring-opening Polymerization of Activated Cyclopropanes - Polymerization of Diethyl 1,1-cyclopropanedicarboxylate By Metallic Sodium

Penelle, J.;Clarebout, G.;Balikdjian, I.
(1994) Polymer Bulletin — Vol. 32, n° 4, p. 395-401 (1994)

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  • Penelle, J.
    Author
  • Clarebout, G.
    Author
  • Balikdjian, I.
    Author
Abstract
Diethyl 1,1-cyclopropanedicarboxylate undergoes ring-opening polymerization under anionic conditions. If the cyclopropane is contaminated by diethyl malonate CH2(COOEt)2, polymerization can be initiated by metallic sodium. The mechanism of this initiation was found to involve an initial reduction of the malonate by sodium to give the salt (EtOOC)2CH(-) Na(+) which acts as the real initiator. Poly(diethyl 1,1-cyclopropane dicarboxylate) is soluble in halogenated solvents and was characterized by GPC, IR, H-1- and C-13-NMR. Molecular weights are low to moderate (typically 10(3)-10(4)) and are compatible with the low monomer / initiator ratios used in these experiments.
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Penelle, J., Clarebout, G., & Balikdjian, I. (1994). Ring-opening Polymerization of Activated Cyclopropanes - Polymerization of Diethyl 1,1-cyclopropanedicarboxylate By Metallic Sodium. Polymer Bulletin, 32(4), 395-401. https://doi.org/10.1007/BF00587880 (Original work published 1994)