Copolymerization of 7-methylenebicyclo[4.1.0]heptane with carbon monoxide initiated by optically active palladium complexes

Daisuke Takeuchi, Ayami Yasuda, Takeshi Okada, Junpei Kuwabara, Kohtaro Osakada, Katsuhiko Tomooka

Research output: Contribution to journalArticlepeer-review

7 Citations (Scopus)

Abstract

Seven Pd-complexes with optically active bis[dihydroxazole]-type ligands promote asymmetric alternating copolymerization of 7-methylenebicyclo[4.1.0] heptane with CO, which produces an optically active polyketone, -[C(=CH 2 )-CO-C 6 H 10 ] n -. The reaction under increased CO pressure (>5 atm) affords a polymer that contains monomer units with the cis-cyclohexane-1,2-diyl group almost exclusively. The polyketone exhibits positive or negative optical rotation depending on the Pd-complex. The highest and lowest [α] D 25 of the polymer obtained are +68.9 and -76.1, respectively. Addition of dibutylcuprate to a solution of the polymer in the presence of Me 3 SiCl transforms the enone groups of the polymer to silyl enol ether groups, which are ozonized to (silyloxy)oxirane moieties.

Original languageEnglish
Pages (from-to)1574-1588
Number of pages15
JournalHelvetica Chimica Acta
Volume89
Issue number8
DOIs
Publication statusPublished - Sep 14 2006
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Biochemistry
  • Drug Discovery
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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