Ruthenium-catalyzed cascade reactions of diynes with norbornadiene -synthesis of norbornene derivatives

Chu Chun Cheng, Chia Sen Change, Yu Lin Hsu, Ting Yu Lee, Ling Chueh Chang, Shih Hsien Liu, Yao Ting Wu

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1 Citation (Scopus)

Abstract

Norbomene derivatives 7-11 were prepared from norbornadiene and the corresponding diynes by Ru-catalyzed [(2+2)+2] cycloaddition and subsequent transfer hydrogenation. The structure and stereochemistry of the cycloadducts were confirmed by X-ray crystal analysis. This procedure provides high diastereoselectivity to generate norbornenes 7-11 in up to 82 % yield. The scope and limitations of this reaction were investigated. Compounds that contained the skeleton of 1,7diaryl-1,6-heptadiynes were suitable starting materials. Additionly, 9h was empolyed in the synthesis of polynorbomene 31 by ring-opening metathesis polymerization (ROMP). The number-average molecular weight (M n) and polymer-distribution index (PDI) of this new polymer were determined to be 28.6 kDa and 1.35, respectively.

Original languageEnglish
Pages (from-to)672-679
Number of pages8
JournalEuropean Journal of Organic Chemistry
Issue number4
DOIs
Publication statusPublished - 2010 Jan 29

All Science Journal Classification (ASJC) codes

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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