Radical Cyclopolymerization of Divinyl Ether. The Microstructure of the Polymer and the Cyclopolymerization Mechanism

Mitsuo Tsukino, Toyoki Kunitake

Research output: Contribution to journalArticle

11 Citations (Scopus)

Abstract

Radical polymerization (AIBN initiator) of divinyl ether yielded partially cyclized, soluble polymers. The pendent vinyloxy group could be completely removed by treating the polymers with 2% hydrochloric acid in methanol. Based on 13C-NMR spectra of these polymers, the original polymer was concluded to contain a five-membered monocyclic unit with the pendent vinyloxy group and a bicyclic unit (dioxobicyclo[3.3.0]octane system) in the 1:1 ratio. The carbon chemical shifts expected for all the possible stereoisomers of these structural units were estimated using a number of model compounds. Apparently a single stereoisomer was formed for both the monocyclic unit (trans ring closure) and the bicyclic unit (with the trans junction). Finally, the steric course of the cyclopolymerization was compared with those of the related systems.

Original languageEnglish
Pages (from-to)387-391
Number of pages5
JournalMacromolecules
Volume12
Issue number3
DOIs
Publication statusPublished - Jan 1 1979

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Ethers
Polymers
Microstructure
Stereoisomerism
Hydrochloric Acid
Chemical shift
Hydrochloric acid
Free radical polymerization
Methanol
Carbon
Nuclear magnetic resonance
vinyl ether

All Science Journal Classification (ASJC) codes

  • Organic Chemistry
  • Polymers and Plastics
  • Inorganic Chemistry
  • Materials Chemistry

Cite this

Radical Cyclopolymerization of Divinyl Ether. The Microstructure of the Polymer and the Cyclopolymerization Mechanism. / Tsukino, Mitsuo; Kunitake, Toyoki.

In: Macromolecules, Vol. 12, No. 3, 01.01.1979, p. 387-391.

Research output: Contribution to journalArticle

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