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

Research Project

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
Project Status Completed (Fiscal Year 2012)
Budget Amount *help
¥3,900,000 (Direct Cost: ¥3,000,000、Indirect Cost: ¥900,000)
Fiscal Year 2012: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
Fiscal Year 2011: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
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 / 酸化 / 環境調和
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.

Report

(3 results)
  • 2012 Annual Research Report   Final Research Report ( PDF )
  • 2011 Research-status Report
  • Research Products

    (33 results)

All 2013 2012 2011 Other

All Journal Article (19 results) (of which Peer Reviewed: 19 results) Presentation (9 results) Book (1 results) Patent(Industrial Property Rights) (4 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

    • Related Report
      2012 Annual Research Report 2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] Facile preparation of aromatic ketones from aromatic bromides and arenes with aldehydes2012

    • Author(s)
      S. Ushijima, S. Dohi, K. Moriyama, and H. Togo
    • Journal Title

      Tetrahedron

      Volume: 68 Pages: 1436-1442

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Aza-Morita-Baylis-Hillman Reaction with Ion-supported Ph3P2012

    • Author(s)
      Y. Imura, N. Shimojuh, K. Moriyama, and H. Togo
    • Journal Title

      Tetrahedron

      Volume: 68 Pages: 2319-2325

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Preparation of N,N-Dimethyl Aromatic Amides from Aromatic Aldehydes with Dimethylamine and Iodine Reagents2012

    • Author(s)
      H. Baba, Moriyama, and H. Togo
    • Journal Title

      Synlett

      Volume: 23 Pages: 1175-1180

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] TEMPO-Mediated Oxidation of Alcohols with Ion-supported (Diacetoxyiodo)benzenes2012

    • Author(s)
      Y. Suzuki, M. Iinuma, K. Moriyama, and H. Togo
    • Journal Title

      Synlett

      Volume: 23 Pages: 1250-1256

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Facile Preparation of Aromatic Esters from Aromatic Bromides with Ethyl Formate or DMF and Molecular Iodine via Aryllithium2012

    • Author(s)
      S. Ushijima, K. Moriyama, and H. Togo
    • Journal Title

      Tetrahedron

      Volume: 68 Pages: 4701-4709

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Practical One-pot Transformation of Electron-rich Aromatics into Aromatic Nitriles with Molecular Iodine and aq. NH3 Using Vilsmeier-Haack Reaction2012

    • Author(s)
      S. Ushijima, K. Moriyama, and H. Togo
    • Journal Title

      Tetrahedron

      Volume: 68 Pages: 4588-4595

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Practical One-pot Preparation of Ketones from Aryl and Alkyl Bromides with Aldehydes and DIH via Grignard Reagent2012

    • Author(s)
      S. Dohi, K. Moriyama, and H. Togo
    • Journal Title

      Tetrahedron

      Volume: 68 Pages: 6557-6564

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Simple and Practical Method for Preparation of [(Diacetoxy)iodo]arenes with Iodoarenes and mCPBA2012

    • Author(s)
      M. Iinuma, K. Moriyama, and H. Togo
    • Journal Title

      Synlett

      Volume: 23 Pages: 2663-2666

    • Related Report
      2012 Annual Research Report
    • 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

    • Related Report
      2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] Swern Oxidation with Ion-supported Sulfoxide2011

    • Author(s)
      D. Tsuchiya, M. Moriyama, H. Togo,
    • Journal Title

      Synlett

      Volume: 8 Pages: 2701-2704

    • Related Report
      2011 Research-status Report
    • Peer Reviewed
  • [Journal Article] One-pot Conversion of Aromatic Bromides i2011

    • Author(s)
      S. Ushijima, K. Moriyama, and H. Togo
    • Journal Title

      Tetrahedron

      Volume: 67 Pages: 958-964

    • Related Report
      2011 Research-status Report
    • Peer Reviewed
  • [Journal Article] Wittig Reaction with Ion-supported Ph3P2011

    • Author(s)
      N. Shimojuh, Y. Imura, K. Moriyama, and H. Togo
    • Journal Title

      Tetrahedron

      Volume: 67 Pages: 951-957

    • Related Report
      2011 Research-status Report
    • Peer Reviewed
  • [Journal Article] Transformation of Aromatic Bromides2011

    • Author(s)
      G. Ishii, K. Moriyama, and H. Togo
    • Journal Title

      Tetrahedron Letter

      Volume: 51 Pages: 2404-2406

    • Related Report
      2011 Research-status Report
    • Peer Reviewed
  • [Journal Article] Direct Transformation of Amides and Esters2011

    • Author(s)
      Y. Suzuki, T. Yosino, K. Moriyama, and H. Togo
    • Journal Title

      Tetrahedron

      Volume: 67 Pages: 3809-3814

    • Related Report
      2011 Research-status Report
    • Peer Reviewed
  • [Journal Article] Iodoarene-mediated α-Tosyloxylation of Ketones2011

    • Author(s)
      A. Tanaka, K. Moriyama, and H. Togo
    • Journal Title

      Synlett

      Volume: 12 Pages: 1853-1858

    • Related Report
      2011 Research-status Report
    • Peer Reviewed
  • [Journal Article] Benzylic-Acyloxylation of Alkylbenzenes2011

    • Author(s)
      H. Baba, K. Moriyama, and H. Togo
    • Journal Title

      Tetrahedron Letters

      Volume: 52 Pages: 4303-4307

    • Related Report
      2011 Research-status Report
    • Peer Reviewed
  • [Journal Article] Facile Transformation of Esters to Nitriles2011

    • Author(s)
      Y. Suzuki, K. Moriyama, and H. Togo
    • Journal Title

      Tetrahedron

      Volume: 67 Pages: 7956-7962

    • Related Report
      2011 Research-status Report
    • Peer Reviewed
  • [Journal Article] Oxidative Intramolecular Bromo-Amination2011

    • Author(s)
      K. Moriyama, Y. Izumisawa, and H. Togo
    • Journal Title

      Journal of Organic Chemistry

      Volume: 76 Pages: 7249-7255

    • Related Report
      2011 Research-status Report
    • Peer Reviewed
  • [Presentation] 芳香環に直結したメチル基からニトリル基へのワンポット変換反応:芳香族ニトリルの    新規合成法2013

    • Author(s)
      土屋大輔、森山克彦、東郷秀雄
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      立命館大学
    • Related Report
      2012 Annual Research Report
  • [Presentation] イオン固定型トリフェニルホスフィンを用いたカルボン酸の環境調和型アミド化反応2013

    • Author(s)
      川越 勇介、森山 克彦、東郷 秀雄
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      立命館大学
    • Related Report
      2012 Annual Research Report
  • [Presentation] 環境調和型新規超原子価ヨウ素の合成と種々の有機合成への利用2013

    • Author(s)
      飯沼雅崇、森山克彦、東郷秀雄
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      立命館大学
    • Related Report
      2012 Annual Research Report
  • [Presentation] 臭化アリール及び臭化アルキルのN,N-ジメチルアミドへのワンポット変換反応の開発2013

    • Author(s)
      石井元規、森山克彦、東郷秀雄
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      立命館大学
    • Related Report
      2012 Annual Research Report
  • [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
    • Related Report
      2012 Final Research Report
  • [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
    • Related Report
      2012 Final Research Report
  • [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
    • Related Report
      2012 Final Research Report
  • [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
    • Related Report
      2012 Annual Research Report
  • [Presentation] ヨウ素を用いた新しい反応の展開

    • Author(s)
      東郷秀雄
    • Organizer
      ハロゲン利用シンポジウム(招待講演)
    • Place of Presentation
      宇都宮大学
    • Related Report
      2011 Research-status Report
  • [Book] 新訂 有機人名反応2011

    • Author(s)
      東郷秀雄
    • Total Pages
      387
    • Publisher
      講談社サイエンティフィック
    • Related Report
      2011 Research-status Report
  • [Patent(Industrial Property Rights)] 芳香族エステル化合物の製造方法及び芳香族アミド化合物の製造方法2012

    • Inventor(s)
      東郷秀雄、土肥壮哉、石井元規、森山克彦、宮本充彦
    • Industrial Property Rights Holder
      東郷秀雄、土肥壮哉、石井元規、森山克彦、宮本充彦
    • Industrial Property Rights Type
      特許
    • Industrial Property Number
      2012-225990
    • Filing Date
      2012-09-11
    • Related Report
      2012 Annual Research Report
  • [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
      2011-183102
    • Filing Date
      2011-08-09
    • Related Report
      2012 Final Research Report
  • [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
      2011-290627
    • Filing Date
      2011-12-21
    • Related Report
      2012 Final Research Report
  • [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
    • Industrial Property Rights Holder
      東郷秀雄
    • Industrial Property Number
      2011-183102
    • Filing Date
      2011
    • Related Report
      2011 Research-status Report

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Published: 2011-08-05   Modified: 2019-07-29  

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