Rapid Preparation of Cycloheptane Ring from 1,2-Diketone and Bis(iodozincio)methane via Oxy-Cope Rearrangement Using Microflow System

• Ryosuke Haraguchi

  Department of Material Chemistry, Graduate School of Engineering, Kyoto University

• Yoshiaki Takada

  Department of Material Chemistry, Graduate School of Engineering, Kyoto University

• Seijiro Matsubara

  Department of Material Chemistry, Graduate School of Engineering, Kyoto University

Abstract

Treatment of 1,6-dialkylhexa-1,5-diene-3,4-diones with bis(iodozincio)methane at −78 °C for several hours gave cis-dialkenylcyclopropane-1,2-diols which rearranged into the zinc alkoxides of cis-5,6-dialkylcyclohepta-3,7-diene-1,3-diol in good yields at room temperature as a one-pot reaction. The reaction should be performed under the careful temperature control. When the reaction was performed using a microflow system, these two-step reactions were able to be performed in a few seconds at room temperature.

Journal

• Chemistry Letters

  Chemistry Letters 41 (6), 628-629, 2012-06

  Oxford University Press (OUP)

Keywords

• General Chemistry

Details

• CRID: 1360846644041837568
• NII Article ID: 10030620589
• NII Book ID: AA00603318
• DOI: 10.1246/cl.2012.628
• ISSN: 13480715
• ISSN: 03667022
• Web Site: https://academic.oup.com/chemlett/article-pdf/41/6/628/55639544/cl.2012.628.pdf
• Data Source:
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  • CiNii Articles
  • KAKEN