Ring-Opening-Closing Alternating Copolymerization of Cyclic Phosphonites with Muconic Acid: Synthesis, Mechanism, and Kinetic Studies

Shiro Kobayaehi, Jun ichi Kadokawa, Hiroshi Uyama, Shin ichiro Shoda, Stefan Landmark

研究成果: Article査読

7 被引用数 (Scopus)

抄録

A new type of alternating copolymerization between cyclic phosphonites (1) with cis,transand cis.cis-muconic acids (2a and 2b) proceeds smoothly without any added catalyst to give copolymers 3a-c having a repeating unit of the ring-opened structure of i and ring-closed structure of 2 (ring-opening-closing alternating copolymerization (ROCAC)). Cyclic phosphonites employed are 2-phenyl-1,3,2-dioxaphospholane (five-membered, 1a), 2-phenyl-1,3,2-dioxaphosphorinane (six-membered, 1b), and 2-phenyl-1,3,2-dioxaphosphepane (seven-membered, 1c). A mechanism which involves a zwitterion intermediate is proposed for the copolymerization. The apparent values of the monomer reactivity ratio were determined as r1a = 0.06 and r2a = 0.00 in DMF at 100 °C. The kinetic study using 1H NMR spectroscopy revealed that the rate constant of the Michael-type addition of 1a to 2a is much larger than that of 1a to 2b.

本文言語English
ページ(範囲)5861-5866
ページ数6
ジャーナルMacromolecules
25
22
DOI
出版ステータスPublished - 1992 10 1

ASJC Scopus subject areas

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

フィンガープリント 「Ring-Opening-Closing Alternating Copolymerization of Cyclic Phosphonites with Muconic Acid: Synthesis, Mechanism, and Kinetic Studies」の研究トピックを掘り下げます。これらがまとまってユニークなフィンガープリントを構成します。

引用スタイル