Alcoholysis of Epoxides Catalyzed by Tetracyanoethylene and Dicyanoketene Acetals.

• Masaki Yukio

  Gifu Pharmaceutical University

• Miura Tsuyoshi

  Gifu Pharmaceutical University

• Ochiai Masahito

  Gifu Pharmaceutical University

Abstract

A typical π-acid tetracyanoethylene and capto-dative olefin dicyanoketene acetals were found to catalyze stereospecific alcoholysis of epoxides at the ambient temperature to 50 °C in good yields. Mildness and significant chemoselectivity of the catalysts were demonstrated by intactness of tetrahydropyranyl ether and ethylene acetal groups. A novel regioselectivity associated with anchimeric assistance of the ethereal group on the side chain was observed in the ring opening reaction of the 1,2-disubstituted epoxides.

Journal

• Bulletin of the Chemical Society of Japan

  Bulletin of the Chemical Society of Japan 69 (1), 195-205, 1996

  The Chemical Society of Japan

Keywords

• General Chemistry

Details

• CRID: 1390001204127589120
• NII Article ID: 10008898718
• NII Book ID: AA00580132
• DOI: 10.1246/bcsj.69.195
• ISSN: 13480634
• ISSN: 00092673
• Web Site: https://academic.oup.com/bcsj/article-pdf/69/1/195/56192313/bcsj.69.195.pdf
• Text Lang: en
• Data Source:
  • JaLC
  • Crossref
  • CiNii Articles
• Abstract License Flag: Disallowed