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Investigation of Reactivities of Electron Deficient Olefins and its Application to Organic Synthesis

Research Project

Project/Area Number 60430008
Research Category

Grant-in-Aid for General Scientific Research (A)

Allocation TypeSingle-year Grants
Research Field 有機化学一般
Research InstitutionKobe University

Principal Investigator

SERA Akira  Kobe University,Faculty of Science, Professor, 理学部, 教授 (90025271)

Co-Investigator(Kenkyū-buntansha) YAMAMURA Kimiaki  Kobe University,College of Liberal Arts, Professor, 教養部, 教授 (60031358)
MASUDA Ryouichi  Kobe University,Faculty of Engineering, Professor, 工学部, 教授 (40031083)
HOJO Masaru  Kobe University,Faculty of engineering,professor, 工学部, 教授 (60031043)
ITOH Kuniaki  Kobe University,Faculty of Science, Assistant, 理学部, 助手 (90144609)
YAMADA Hiroaki  Kobe University,Faculty of Science, Assistant Professor, 理学部, 助教授 (90030767)
Project Period (FY) 1985 – 1987
Project Status Completed (Fiscal Year 1987)
Budget Amount *help
¥25,000,000 (Direct Cost: ¥25,000,000)
Fiscal Year 1987: ¥1,000,000 (Direct Cost: ¥1,000,000)
Fiscal Year 1986: ¥3,000,000 (Direct Cost: ¥3,000,000)
Fiscal Year 1985: ¥21,000,000 (Direct Cost: ¥21,000,000)
KeywordsTitanium trichloride reduction / Electroreduction / Nitroolefin / Dicyanoolefin / Nitrile / High pressure cycloaddition / チオアセタール化触媒 / ニトロオレフィン / シアノオレフィン / 電解還元 / 置換インデン合成 / アザブタジエン / 三塩化チタン / ピロール / ジビニルアミン / イソオキサゾール / ピラゾール / ヘテロ環合成
Research Abstract

1. Titanium Trichloride Mediated Reduction of Nitro-, and Dicyanoolefins:
Aqueous titanium trichloride was found to reduce nitorolefins to pyrroles and/or divinyl amines in moderate yields. Dicyanoolefins were also reduced to give five menbered cyclic eneaminonitriles.
2. Electroreduction of Nitroolefins in the Presence of Titanium Tetrachloride:
Electroreduction of nitroolefins was achieved in the presence of titanium tetrachloride in DMF to yield corresponding nitriles in high yields. Nitroolefins can be easily prepared by means of condensation of aldehydes with nitromethan, and hence the present reduction offers a new synthetic method of one carbon elongated nitriles from easily available aldehydes.
3. High Pressure cycloaddition of Furan
The Diels-Alder reaction of furan with dialkyl acetxymethylenemalonate did not proceed at conventional conditions. However, the reaction took place under high pressure of 1 GPa to give an adduct. 7-oxabicyclo[2.2.1]heptene derivative, from which a precursor of C-ribonucleoside was synthesized stereospecifically in a high yield.

Report

(3 results)
  • 1987 Final Research Report Summary
  • 1986 Annual Research Report
  • 1985 Annual Research Report

Research Products

(90 results)

All Other

All Publications (90 results)

  • [Publications] H.Yamada: Bull. Chem. Soc. Jpn.58. 1341-1342 (1985)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] K.Matsumoto: Synthesis. 1-26 (1985)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] K.Matsumoto: Synthesis. 999-1027 (1985)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] K.Itoh: Bull. Chem. Soc. Jpn.59. 479-482 (1986)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] K.Yamamura: Bull. Chem. Soc. Jpn.3699-3701 (1986)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] A.Sera: Synthesis. 631-633 (1986)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] A.Sera: Heterocycles. 697-702 (1986)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] H.Yamada: Chemistry Lett.1397-1398 (1986)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] K.Matsumoto: Chemistry Lett.805-806 (1986)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] E.M.Schulman: J. Am. Chem. Soc.109. 7209-7210 (1987)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] A.Sera: J. Org. Chem.53. (1988)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] A.Sera: J. Org. Chem.53. (1988)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Y.Kamitori: Chemistry Lett.253-254 (1985)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Y.Kamitori: Tetrahedron Lett.26. 4767-4770 (1985)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Y.Kamitori: Synthesis. 340-342 (1986)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] M.Hojo: Synthesis. 137-139 (1986)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Y.Kamitori: J. Org. Chem.51. 1427-1431 (1986)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] M.Hojo: Tetrahedron Lett.27. 353-356 (1986)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] M.Hojo: Synthesis. 1013-1014 (1986)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] M.Hojo: Synthesis. 1016-1017 (1986)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] H.Hojo: Tetrahedron Lett.28. 6199-6170 (1987)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] M.Hojo: J. Org. Chem.53. (1988)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] M.Hojo: J. Org. Chem.53. (1988)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] M.Hojo: J. Org. Chem.53. (1988)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] M.Hojo: J. Org. Chem.53. (1988)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] H.Miyake: Bull. Chem. Soc. Jpn.59. 89-91 (1986)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] K.Yamamura: Bull. Chem. Soc. Jpn.59. 207-214 (1986)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] K.Yamamura: J. Org. Chem.51. 251-253 (1986)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] H.Miyake.: Tetrahedron Lett.27. 3025-3028 (1986)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] K.Yamamura: Chemistry Lett.(1988)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] K.Yamamura: Chemistry Lett.(1988)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] K.Yamamura: Bull. Chem. Soc. Jpn.61. (1988)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] K.Yamamura: Chemistry Lett.(1988)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] R.Goto: "Chemistry of Monosaccharides." Maruzene Publisher, 280 (1988)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] H. Yamada: "Pressure-induced Proton NMR Chemical Shift of Some Simple Hydrocarbon Molecules in Hexane Solution. Marked Low Field Shift of Ethynyl Proton Resonance." Bull. Chem. Soc. Jpn.,. 58. 1341-1342 (1985)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] K. Matsumoto: "Organic Synthesis under High Pressure I." Synthesis. 1-26 (1985)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] K. Matsumoto: "Organic Synthesis under High Pressure II." Synthesis. 999-1027 (1985)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] K. Itoh: "Addition Reaction of 1,4-Dibromo-2,5-piperezinedione with 3,4-Dihydro-2H-pyran." Bull. Chem. Soc. Jpn.,. 59. 479-482 (1986)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] K. Yamamura: "Formation of 2-Substituted 1,3-Diphenylindenses by an N-Bromosuccinimide Promoted Dehydrocyclization of 2-Substituted 1,3,3-Triphenyl-1-propenes." Bull. Chem. Soc. Jpn.,. 59. 3699-3701 (1986)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] A. Sera: "Titanium Trichloride Mediated Reduction of Nitrostyrenes." Heterocycles. 24. 697-702 (1986)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] H. Yamada: "Pressure Effect on the P-H and ^<13>C-H Spin-Spin Coupling Constants in Diphenylphosphine and Diphenylmethane-1-^<13>C in Chloroform." Chemistry Lett.1397-1398 (1986)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] K. Matsumoto: "Crystal Structure of a Novel 1;2 Adduct from [2.2]Paracyclophane and N-Methylmaleimide." Chemistry Lett.805-806 (1986)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] A. Sera: "A Facile Synthesis of Nitriles from 1-Nitro-1-alkenes by Electroreduction." Synthesis. 631-633 (1986)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] E. M. Schulman: "Pressure Effect of the ^1H NMR Spectra of Organic Compounds in the Presence of Lanthanide Shift Reagents. A Formally Associative Process Characterized by Volume Expansion." J. Am. Chem. Soc.109. 7209-7210 (1987)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] A. Sera: "High Pressure Asymmetric Michael Addition of Thiols, Nitromethane, and Methyl oxoindancarboxylate to Enones." J. Org. Chem.53. (1988)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] A. Sera: "High Pressure Mediated Diels-Alder Reaction of Furan with Dialkyl Acetoxymethylenemalonates." J. Org. Chem.53. (1988)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Y. Kamitori: "Sodium Sulfide as a Selective Reduction Reagent for Aldehydes to Alcohols. Use of Alumina as an Effective Catalyst." Chemistry Lett.253-254 (1985)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Y. Kamitori: "Alumina as a Versatile Catalyst for the Selective Acetalization of Aldehydes." Tetrahedron Lett.26. 4767-4770 (1985)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Y. Kamitori: "A New Convenient Synthetic Method for 3-Allyl-1,1,1-trifluoroacetylacetone and its Derivatives." Synthesis. 340-342 (1986)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] M. Hojo: "A New Facile and Convenient Synthesis of 2-Oxo-3-alkenoic Acids and Esters." Synthesis. 137-139 (1986)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Y. Kamitori: "Selective Protection of Carbonyl Compounds. Silica Gel Treated with Thionyl Chloride as an Effective Catalyst for Thioacetalization." J. Org. Chem.51. 1427-1431 (1986)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] M. Hojo: "Electrophilic Substitutions of Olefinic Hydrogens: Acylation of 1,1-Bisalkylthio-1,3-alkadienes and trans-N-Acetyl-N-isopropyl-1-amino-1,3-butadiene." Tetrahedron Lett.27. 353-356 (1986)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] M. Hojo: "A Useful One-step Synthesis of beta-Thioacetylvinyl Ethers and Trihaloacetylketene Acetals." Synthesis. 1013-1014 (1986)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] M. Hojo: "A Convenient Synthetic Method for beta-Alkoxy- and beta-phenoxyacrylic Acids and 3,4-Dihydro-2H-pyran-5- and 2,3-Dihydrofuran-4-carboxylic Acids." Synthesis. 1016-1017 (1986)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] M. Hojo: "Nucleophilic Nitrogen-Nitrogen Exchange Reaction at Aromatic Carbon Atoms--Reaction of N,N-Dimethyl-2,4-bistrifuluoroacetyl-1-naphthylamine with Various Amines." Tetrahedron Lett.28. 6199-6200 (1987)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] M. Hojo: "Electrophilic Substitution Reaction at Azomethine Carbon Atoms. Acylation of Aliphatic Aldehyde Hydrazones." J. Org. Chem.53. (1988)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] M. Hojo: "Electrophilic Substitution Reaction at Azomethine Carbon Atoms. Reaction of Aromatic Aldehyde Hydrazones with Trifluoroacetic Anhydride." J. Org. Chem.53. (1988)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] M. Hojo: "A Convenient Synthetic Method for 6-Trifluoromethyl-5-aryl-3,6-dihydro-2H-1,3,4-oxadiazine." J. Org. Chem.53. (1088)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] M. Hojo: "Isolation and Reaction of New Aromatic Dication-4-Thioniapyridinium Dication." J. Org. Chem.53. (1988)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] H. Miyake: "Replacement of the Acrivated Nitro Group by a phenylthio Group." Bull. Chem. Soc. Jpn.59. 89-91 (1986)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] K. Yamamura: "Three-Dimensionally-Modified Tetracyanoquinodimethanes and their Charge-Transfer Complexes with Tetrathiafulvalene Derivatives Having a Wide Range of Ionicity." Bull. Chem. Soc. Jpn.59. 207-214 (1986)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] K. Yamamura: "Synthesis and Properties of Cyclohexa[c,d]perylenium Tetrafluoroborate. A Homologue of the Phenalenium Ion." J. Org. Chem.51. 251-253 (1986)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] H. Miyake: "Lewis Acid Catalyzed Substitution of Allylic Nitro Compounds with Cyanotrimethylsilane." Tetrahedron Lett.27. 3025-3028 (1986)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] K. Yamamura: "Substituent Effect in 9,10-Dihydro-9,10-o-Benzenoanthracene-1,4-diones on the Half-wave Potentioals." Chemistry Lett.(1988)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] K. Yamamura: "Conformational Adoptation. Electrondonating Capacities of Methyl and Methoxy Groups." Chemistry Lett.submitted (1988)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] K. Yamamura: "Free Radical Addition of Thiophenol to 3-Substituted 1-Alkynes with or without Migration of the Substituents." Bull. Chem. Soc. Jpn.61. submitted (1988)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] K. Yamamura: "Intramolecular Charge-Transfer Transition in 5,8-Oxa-5,8-dihydro-[6,7]naphthonaphthalene-1,4-diones." Chemistry Lett.submitted (1988)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] R. Goto: Chemistry of Monosaccharides. Maruzen Publisher, 280 (1988)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] A.Sera: Heterocycles. 24. 697-702 (1986)

    • Related Report
      1986 Annual Research Report
  • [Publications] A.Sera: Chemistry Letters. (1987)

    • Related Report
      1986 Annual Research Report
  • [Publications] H.Yamaka: Chemistry Letters. 1397-1398 (1986)

    • Related Report
      1986 Annual Research Report
  • [Publications] K.Itoh: Bull.Chem.Soc.Jpn.59. 478-482 (1986)

    • Related Report
      1986 Annual Research Report
  • [Publications] T.Miyazawa: Tetrahebron Letters. 28. (1987)

    • Related Report
      1986 Annual Research Report
  • [Publications] A.Sera: Synthesis. (1987)

    • Related Report
      1986 Annual Research Report
  • [Publications] M.Hojo: Tetrahedron Letters. 27. 353-356 (1986)

    • Related Report
      1986 Annual Research Report
  • [Publications] Y.Kamitori: J.Org.Chem.51. 1427-1431 (1986)

    • Related Report
      1986 Annual Research Report
  • [Publications] M.Hojo: Synthesis. 137-139 (1986)

    • Related Report
      1986 Annual Research Report
  • [Publications] Y.Kamitori: Synthesis. 340-342 (1986)

    • Related Report
      1986 Annual Research Report
  • [Publications] M.Hojo: Synthesis. 1013-1014 (1986)

    • Related Report
      1986 Annual Research Report
  • [Publications] M.Hojo: Synthesis. 1016-1017 (1986)

    • Related Report
      1986 Annual Research Report
  • [Publications] H.Miyake: Bull.Chem.Soc.Jpn.59. 89-91 (1986)

    • Related Report
      1986 Annual Research Report
  • [Publications] K.Yamamura: Bull.Chem.Soc.Jpn.59. 207-214 (1986)

    • Related Report
      1986 Annual Research Report
  • [Publications] K.Yamamura: J.Org.Chem.51. 251-253 (1986)

    • Related Report
      1986 Annual Research Report
  • [Publications] H.Miyake: Tetrahedron Letters. 27. 3025-3028 (1986)

    • Related Report
      1986 Annual Research Report
  • [Publications] K.Yamamura: Bull.Chem.Soc.Jpn.59. 3699-3701 (1986)

    • Related Report
      1986 Annual Research Report
  • [Publications] Synthesis. 11. (1985)

    • Related Report
      1985 Annual Research Report
  • [Publications] Bull.Chem.Soc.Jpn.59-2. (1986)

    • Related Report
      1985 Annual Research Report
  • [Publications] Heterocvcles. 24-3. (1986)

    • Related Report
      1985 Annual Research Report
  • [Publications] Tetrahedron Lett.26-39. (1985)

    • Related Report
      1985 Annual Research Report
  • [Publications] Tetrahedron Lett.27-3. (1986)

    • Related Report
      1985 Annual Research Report

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Published: 1987-03-30   Modified: 2016-04-21  

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