• Search Research Projects
  • Search Researchers
  • How to Use
  1. Back to previous page

Development of New Synthetic Methods by Use of Heteroatom Elements and their Application to Organic Synthesis

Research Project

Project/Area Number 07505009
Research Category

Grant-in-Aid for Scientific Research (A)

Allocation TypeSingle-year Grants
Section試験
Research Field Synthetic chemistry
Research InstitutionOsaka University

Principal Investigator

SONODA Noboru  Osaka University, Faculty of Engineering, Department of Applied Chemistry, Professor, 工学部, 教授 (20083983)

Co-Investigator(Kenkyū-buntansha) RYU Ilhyong  Osaka University, Faculty of Engineering, Department of Applied Chemistry, Assoc, 工学部, 助教授 (80210821)
OGAWA Akiya  Osaka University, Faculty of Engineering, Department of Applied Chemistry, Assoc, 工学部, 助教授 (30183031)
KAMBE Nobuaki  Osaka University, Faculty of Engineering, Department of Applied Chemistry, Assoc, 工学部, 助教授 (60144432)
Project Period (FY) 1995 – 1996
Project Status Completed (Fiscal Year 1996)
Budget Amount *help
¥35,100,000 (Direct Cost: ¥35,100,000)
Fiscal Year 1996: ¥4,800,000 (Direct Cost: ¥4,800,000)
Fiscal Year 1995: ¥30,300,000 (Direct Cost: ¥30,300,000)
Keywordsheteroatom elements / organolithium compounds / selenium catalyzed carbonylation / selenoesters / carbon monoxide / organoselenium compounds / radical carbonylation / イミドイルラジカル / 炭素-炭素結合生成反応 / テルリドの付加反応 / 交換反応 / 有機リチウム化合物 / セレン触媒 / ラジカルカルボニル化
Research Abstract

The aim of this project is to develop the new synthetic reactions based on the characteristics chemical properties of heteroatom elements and to apply these reactions to organic synthesis. The representative results were summarized below. (1) Diorganyl tellurides add to carbon-carbon triple bonds in the presence of a radical initiator to give corresponding vinylic tellurides. By the use of this reaction, a stereoselective synthetic method of divinyl tellurides has been developed. (2) A variety of organolithium compounds have been generated by tellurium-lithium exchange reaction and used for carbon-carbon forming reactions. Kinetic studies of metalloid-lithium exchange, such as I-Li, Se-Li, Te-Li, Sn-Li exchange, have been performed and the relative rates were determined by competitive experiments. (3) Unique cyclic diureas have been synthesized by selenium catalyzed carbonylation of tetraamines with carbon monoxide and their structures were determined by X-ray crystal structure analysis. By the theoretical calculations of selenium catalyzed carbonylation of amines, two possible reaction pathways for the generation of carbonyl selenide, which play an important role as the key intermediate, have been proposed. (3) A new preparative method of selenoesters from organolithiums, selenium, carbon monoxide, and alkyl halides has been developed. The use of isonitriles instead of carbon monoxide affords selenoimidates in good yields under similar conditions. (4) As the synthetic application of radical carbonylation methodology, we developed photoinitiated carbonylation of organoselenium compounds and double carbonylation of halogen substituted alkenes which gives diketones or ketoaldehydes via radical cyclization.

Report

(3 results)
  • 1996 Annual Research Report   Final Research Report Summary
  • 1995 Annual Research Report
  • Research Products

    (27 results)

All Other

All Publications (27 results)

  • [Publications] Noboru Sonoda 他4名: "Carbonylation of Acidic Hydrocarbons with Selenium and Carbon Monoxide. A Novel Method for Synthesis of Selenol Esters" J. Am. Chem. Soc.118(34). 8160-8161 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Noboru Sonoda 他4名: "Group Transfer Carbonylations : Photoinduced Alkylative Carbonylation of Alkenes Accompanied by Phenylselenenyl Transfer" J. Org. Chem.61(18). 6396-6403 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Noboru Sonoda 他4名: "Reaction of 2,6-Xylyl Isoselenocyanate with Organolithium Compounds" Tetrahedron. 52(37). 12165-12176 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Noboru Sonoda 他6名: "Free Radical Mediated Double Carbonylations of Alk-4-enyl Iodides" J. Am. Chem. Soc.118(43). 10670-10671 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Noboru Sonoda 他2名: "A Theoretical Study on the Generation Process of Carbonyl Selenide in Selenium Catalyzed Carbonylation of Amines" Chem. Lett.(2). 155-156 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Noboru Sonoda 他5名: "Synthesis and Structures of Tricyclic Diureas" J. Org. Chem.60(21). 7058-7062 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Hajime Maeda, Shin-ichi Fujiwara, Tsutomu Shin-Ike, Nobuaki Kambe, Noboru Sonoda: "Carbonylation of Acidic Hydrocarbons with Selenium and Carbon Monoxide. A Novel Method for Synthesis of Selenol Esters" J.Am.Chem.Soc.118(34). 8160-8161 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Ilhyong Ryu, Hideo Muraoka, Nobuaki Kambe, Mitsuo Komatsu, Noboru Sonoda: "Group Transfer Carbonylations : Photoinduced Alkylative Carbonylation of Alkenes Accompanied by Phenylselenenyl Transfer" J.Org.Chem.61(18). 6396-6403 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Hajime Maeda, Nobuaki Kambe, Noboru Sonoda, Shin-ichi Fujiwara, Tsutomu Shin-Ike: "Reaction of 2,6-Xylyl Isoselenocyanate with Organolithium Compounds" Tetrahedron. 52(37). 12165-12176 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Shinji Tsunoi, Ilhyong Ryu, Sumiaki Yamasaki, Hiroshi Fukushima, Minoru Tanaka, Mitsuo Komatsu, Noboru Sonoda: "Free Radical Mediated Double Carbonylations of Alk-4-enyl Inodides" J.Am.Chem.Soc.118(43). 10670-10671 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Shinji Tsunoi, Ilhyong Ryu, Hideo Muraoka, Minoru Tanaka, Mitsuo Komatsu, Noboru Sonoda: "Stannylformylation of Vinylcyclopropanes Accompanied by Radical Ring-Opening" Tetrahedron Lett.37(37). 6729-6732 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Jun Terao, Nobuaki Kambe, Noboru Sonoda: "A New Preparative Method of Alkenylaluminum Reagents via Tellurium-Aluminum Exchange Reactions" Synlett. (8). 779-780 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Jun Terao, Nobuaki Kambe, Noboru Sonoda: "Tellurium-Zinc Exchange Reaction. A New Praparative Method of Alkenylzinc Reagents" Tetrahedron Lett.37(27). 4741-4744 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Wladmir Ferraz de Souza, Nobuaki Kambe, Noboru Sonoda: "A Theoretical Study on the Generation Process of Carbonyl Selenide in Selenium Catalyzed Carbonylation of Amines" Chem.Lett.(2). 155-156 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Takahiro Kanda, Shinzi Kato, Nobuaki Kambe, Yasuhisa Kohara, Noboru Sonoda: "Relative Rates, Relative Activation Parameters and Substituent Effects of Lithium-Metalloid Exchange Reactions" J.Phys.Org.Chem.9(1). 29-34 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Wladmir Ferraz de Souza, Nobuaki Kambe, Zhen Ji Jin, Nobuko Kanehisa, Yasushi Kai, Noboru Sonoda: "Synthesis and Structures of Tricyclic Diureas" J.Orh.Chem.60(21). 7058-7062 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Takahiro Kanda, Shinzi Kato, Takushi Sugino, Nobuaki Kambe, Akiya Ogawa, Noboru Sonoda: "3,4-Dihydroisocoumarins from alpha-Bromo-o-tolunitrile and Ketones or Aldehydes" Synthesis. (9). 1102-1106 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Takahiro Kanda, Yoshio Ando, Shinzi Kato, Nobuaki Kambe, Noboru Sonoda: "A One-pot Conversion of Propargylic Bromides to Alleyl-, Propargyl-and 1-Propynyllithiums" Synlett. (7). 745-747 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Noboru Sonoda 他4名: "Carbonylation of Acidic Hydrocarbons with Selenium and Carbon Monoxide.A Novel Method for Synthesis of Selenol Esters" J.Am.Chem.Soc.118(34). 8160-8161 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] Noboru Sonoda 他4名: "Group Transfer Carbonylations:Photoinduced Alkylative Carbonylation of Alkenes Accompanied by Phenylselenenyl Transfer" J.Org.Chem.61(18). 6396-6403 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] Noboru Sonoda 他4名: "Reaction of 2,6-Xylyl Isoselenocyanate with Organolithium Compounds" Tetrahedron. 52(37). 12165-12176 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] Noboru Sonoda 他6名: "Free Radical Mediated Double Carbonylations of Alk-4-enyl Iodides" J.Am.Chem.Soc.118(43). 10670-10671 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] Noboru Sonoda 他5名: "Stannylformylation of Vinylcyclopropanes Accompanied by Radical Ring-Opening" Tetrahedron Lett.37(37). 6729-6732 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] Takahiro Kanda: "A One-pot Conversion of Propargylic Bromides to Allenyl-,Propargyl-and 1-Propynyllithiums" SYNLETT. 7. 745-747 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] Akiya Ogawa: "The First Example of Transition-Metal-Catalyzed Thioformylation of Acetylenes with Aromatic Thiols and Carbon Monoxide" J.Am.Chem.Soc.177. 7564-7565 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] Akiya Ogawa: "A New Reduction System by the Combintion of Lanthanoid Metals(Ln)and Lnl_2:Deoxygenative Coupling of Amides to vic-Diaminoalkenes" Appl.Org.Anomet.Chem.9. 461-466 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] Takahiro Kanda: "3,4-Dihydroisocoumrins from α-Bromo-o-tolunitrile and Ketones or aldehydes" Synthesis. 9. 1102-1106 (1995)

    • Related Report
      1995 Annual Research Report

URL: 

Published: 1995-04-01   Modified: 2016-04-21  

Information User Guide FAQ News Terms of Use Attribution of KAKENHI

Powered by NII kakenhi