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2012 Fiscal Year Final Research Report

Synthetc Study and Reuse of IonSupported Methyfoxdes for Swern daton wthout Unpleasant Odor

Research Project

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Project/Area Number 23655142
Research Category

Grant-in-Aid for Challenging Exploratory Research

Allocation TypeMulti-year Fund
Research Field Environmental chemistry
Research InstitutionChiba University

Principal Investigator

TOGO Hideo  千葉大学, 大学院・理学研究科, 教授 (60217461)

Project Period (FY) 2011 – 2012
KeywordsSwern酸化反応 / アルコール / アルデヒド / ケトン / Corey-Kim酸化反応 / イオン固定型メチルスルホキシド / イオン固定型メチルスルフィド / 再生再利用
Research Abstract

The Swern oxidation of various benzylic and allylic alcohols, primary alcohols, and secondary alcohols with two ion-supported methyl sulfoxides C_6and C_<10>, and oxalyl chloride in the presence of triethylamine in dichloromethane, followed by simple diethyl ether extraction of the reaction mixture, gave the corresponding aldehydes and ketones, respectively, in good yields with high purity. Similarly, the Corey-Kim oxidation of various benzylic and allylic alcohols, primary alcohols, and secondary alcohols with two ion -supported methyl sulfides C_6 and_<10>, andCN-chlorosuccinimide in the presence of triethylamine in dichloromethane, followed by simple diethyl ether extraction of the reaction mixture, furnished the corresponding aldehydes and ketones, respectively, in good yields with high purity. Both reactions did not produce any unpleasant odor at all. In the Swern oxidation, ion-supported methyl sulfides were recovered in high yields and could be re-oxidized to produce ion-supported methyl sulfoxides C6andC_<10>, for reuse in the same oxidation. In the Corey-Kim oxidation, ion-supported methyl sulfidesC_6 and C_<10> were recovered in high yields and could be also reused for the same oxidation.

  • Research Products

    (7 results)

All 2012 2011

All Journal Article (2 results) (of which Peer Reviewed: 2 results) Presentation (3 results) Patent(Industrial Property Rights) (2 results)

  • [Journal Article] Efficient Swern Oxidation and Corey-Kim Oxidation with Ion-supported Methyl Sulfoxides and Methyl Sulfides2012

    • Author(s)
      Daisuke Tsuchiya, Masayuki Tabata, Katsuhiko Moriyama, Hideo Togo
    • Journal Title

      Tetrahedron

      Volume: 68 Pages: 6849-6855

    • Peer Reviewed
  • [Journal Article] Swern Oxidation of Alcohols with Ion -supported Methyl Sulfoxide and Oxalyl Chloride2011

    • Author(s)
      Daisuke Tsuchiya, Katsuhiko Moriyama, Hideo Togo
    • Journal Title

      Synlett

      Volume: 23 Pages: 2701-2704

    • Peer Reviewed
  • [Presentation] イオン固定型メチルスルホキシド及びスルフィドを用いたアルコールのSwern酸化反応とCorey-Kim 酸化反応2012

    • Author(s)
      土屋大輔、田端真之、森山克彦、東郷秀雄
    • Organizer
      第101回有機合成化学シンポジウム
    • Place of Presentation
      早稲田大学
    • Year and Date
      20121110-11
  • [Presentation] イオン固定型メチルスルフィドを用いたCorey-Kim 酸化反応2012

    • Author(s)
      土屋大輔、森山克彦、東郷秀雄
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      慶応義塾大学
    • Year and Date
      20120325-0328
  • [Presentation] イオン固定型メチルスルホキシドを用いたSwren酸化反応2012

    • Author(s)
      田端真之、土屋大輔、森山克彦、東郷秀雄
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      慶応義塾大学
    • Year and Date
      20120325-0328
  • [Patent(Industrial Property Rights)] イミダゾリウム部位を有する新規スルホキシド誘導体2011

    • Inventor(s)
      東郷秀雄、土屋大輔、田端真之、森山克彦
    • Industrial Property Rights Holder
      東郷秀雄、土屋大輔、田端真之、森山克彦
    • Industrial Property Number
      特許、特願2011-183102
    • Filing Date
      2011-08-09
  • [Patent(Industrial Property Rights)] イミダゾリウム塩部位を有するスルフィド誘導体を用いるアルコールの酸化法2011

    • Inventor(s)
      東郷秀雄、土屋大輔、田端真之、森山克彦
    • Industrial Property Rights Holder
      東郷秀雄、土屋大輔、田端真之、森山克彦
    • Industrial Property Number
      特許、特願2011-290627
    • Filing Date
      2011-12-21

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Published: 2014-09-25  

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