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Ring-opening polymerization of activated cyclopropanes: polymerization of diethyl 1,1-cyclopropanedicarboxylate by metallic sodium

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Summary

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,1H- and13C-NMR. Molecular weights are low to moderate (typically 103–104) and are compatible with the low monomer/initiator ratios used in these experiments.

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References

  1. Hall HK, Snow LG (1984) Ring-opening Polymerizations via Carbon-Carbon σ-Bond Cleavage. In: Ivin KJ, Saegusa T (eds) Ring-Opening Polymerization. Elsevier, London

    Google Scholar 

  2. Cho I, Kim J-B (1980) J. Polym. Sci., Part A: Polym. Chem. 18: 3053

    Google Scholar 

  3. Cho I, Ahn K-D (1979) J. Polym. Sci., Part A: Polym. Chem. 17: 3183

    Google Scholar 

  4. Szabo GT, Aranyosi K, Csiba M, Toke L (1987) Synthesis 738

  5. Stewart JM, Westberg HH (1965) J. Org. Chem. 30: 1951

    Google Scholar 

  6. Zefirov NS, Kuznetsova TS, Kozhushkov SI, Surmina LS, Raschupkina ZA (1983) Zh. Org. Khim. (Engl. Transl.) 19: 474

    Google Scholar 

  7. Bone WA, Perkin WH (1895) J. Chem. Soc. 67: 108

    Google Scholar 

  8. Harsanyi K, Heuszman J, Toke L, Felmeri J, Nemeth S, Bitter I (1984) Hung. Teljes HU 32, 794; (1985) Chem. Abstr. 102: 131581n

  9. Bremser W, Franke B, Wagner H (1982) Chemical Shift Ranges in Carbon-13 NMR Spectroscopy. Verlag Chemie, Weinheim

    Google Scholar 

  10. Schaefer JP, Bloomfield JJ (1967) Org. React. 15: 1

    Google Scholar 

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Authors and Affiliations

  1. Laboratoire Cinétique et Macromolécules, Département de Chimie, Université Catholique de Louvain, Place L. Pasteur 1, B-1348, Louvain-la-Neuve, Belgium

    Jacques Penelle, Gilles Clarebout & Isabelle Balikdjian

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  1. Jacques Penelle
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  2. Gilles Clarebout
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  3. Isabelle Balikdjian
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Penelle, J., Clarebout, G. & Balikdjian, I. Ring-opening polymerization of activated cyclopropanes: polymerization of diethyl 1,1-cyclopropanedicarboxylate by metallic sodium. Polymer Bulletin 32, 395–401 (1994). https://doi.org/10.1007/BF00587880

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  • DOI: https://doi.org/10.1007/BF00587880

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