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1989 Fiscal Year Final Research Report Summary

REACTIVITY CONTROL IN ORGANIC CHEMISTRY

Research Project

Project/Area Number 63303002
Research Category

Grant-in-Aid for Co-operative Research (A)

Allocation TypeSingle-year Grants
Research Field 有機化学一般
Research InstitutionKYOTO UNIVERSITY

Principal Investigator

HAYAMI Jun-ichi  COLLEGE OF LIBERAL ARTS AND SCIENCES, CHEMISTRY, PROFESSOR, 教養部, 教授 (30025283)

Co-Investigator(Kenkyū-buntansha) TANIGUCHI Hiroshi  KYUSHU UNIV. APPL.CHEM.PROF., 工学部, 教授 (10037715)
MOROKUMA Keiji  MOLECULAR SCIENCE INST.PROF., 教授 (40111083)
SAKURAI Hideki  TOHOKU UNIV. CHEMISTRY PROF., 理学部, 教授 (70025873)
MARUYAMA Kazuhiro  KYOTO UNIV. CHEMISTRY PROF., 理学部, 教授 (90025263)
TSUNO Yuho  KYUSHU UNIV. CHEMISTRY PROF., 理学部, 教授 (10029845)
Project Period (FY) 1988 – 1989
KeywordsPHYSICAL ORGANIC CHEMISTRY / REACTIVITY / REACTIVITY CONTROL / MOLECULAR INTERACTION / SUBSTITUENT EFFECT / HETEROATOM CHEMISTRY / THEORETICAL CHEMISTRY / ORGANOMETALLIC CHEMISTRY
Research Abstract

Twenty four leading physical organic chemists in representative universities and research institutions made up a cooperative research project team.
The major aim of the team is to try to establish a comprehensive understanding of the factors governing the reactivity of organic compounds in quantitative sense as far as possible. Approaches are made from the stand points of 1)transmission of the effects of the structural change: 2)chemistry of reactive chemical species and identities: 3)detection and quantilization of interspeclies interaction: 4)identification and characterization of the reaction field covering the topics of molecular aggregates and clusters.
Members of the project team are involved both the research of the individual field and the discussion-cooperation of the interlocking aspects of the interesting problems. The results are exemplified by the 192 references in the varieties of the approach which are cited in the Japanese text of the final research report. Representative results are a)the elucidation of the degree of the electron demand common to organic cationic species and transition state; b)elucidation of the importance of the molecular association in the nucleophilic organic reactions such as Griganard Reaction, Wittig Reaction, S_NAr Reaction etc. through both experimental and theoretical approach.

  • Research Products

    (48 results)

All Other

All Publications (48 results)

  • [Publications] Junーichi HAYAMI,et.al.: "An Enatioselective Role of a Ternary Complex in the Asymmetric “Hydride"Transfer Reaction between NAD(P)H Model Compound and 5ーDeazaflavin Possessing Planar Chirality." Tetrahedron Letters. (1990)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Shinya NISHIDA,et.al.: "Reactions of Some Cyclopropanes activated by a SpiroーLinked Fluorene.Importance of Electronic Mathing of a Reacting Partner in Thermal Cycloaddition with TCNE and RingーOpening Dehydrogenation with DDO." J.Org.Chem.54. 3859-3868 (1989)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Mitsuo KIRA,et.al.: "Highly Stereoselective Allylation of Aldehydes with Pantacoordinate AllylーSilicates in Hydroxic Media.Discrimination between Linear and Alphaーbranched Alkanols." J.Am.Chem.Soc.112. 257 (1989)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Naoki INAMOTO,et.al.: "Relationship between Substetuent Electronegativity and Field Parameter in the Aliphatic Series,Introduction of Charge Separation Parameter( )." J.Phys.Org.Chem. 3. 2 (1990)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Hiizu IWAMURA,et.al.: "Magnetic Coupling of Two Triplet Phenylnitrene Units Joined through an Acetylenic or Diacetylenic Linkage." Mol.Cryst.Lig.Cryst.176. 33-48 (1989)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Hideyuki MATSUMOTO,et.al.: "Photolysis of Cyclotetrasilanes,a Remarkable Dependence on Molecular Structure." J.Chem.Soc.Faraday Trans.I. 85. 2369-2379 (1989)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Yasunori HASE,et.al.: "How to Determine the Force Constants of MM2 Force Field in a Consistent Way?" Chemistry Letters. 1507-1510 (1989)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Yoshiaki HORIGUDHI,et.al: "Does Me_3SiCl Activate Condugate Addition of Copper Reagents as a Lewis Acid?" Tetrahedron Letters. 7087 (1989)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Nobuaki KOGA,et.al: "An Initio Molecular Orbital Studies of Intermediates and Transition States of Organometallic Elementary Reactions and Homogeneous Catalytic Cycles." Topics in Physical Organometallic Chemistry. 3. 1 (1989)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] M.KITAMUTA,et.al.: "Enantioselective Addition of Dialkylzincs to Aldehydes Promoted by Chiral Amino Alcohols.Mechanism and Nonlinear Effect." J.Am.Chem.Soc.111. 4028 (1989)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Kaoru NAKAMURA,et.al: "Determination of the Configuration of Diastereomers of 2ーAlkylー3ーhydroxybutanotes with Gas Chromatography." Bull.Chem.Soc.Jpn.63. 298-300 (1990)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Kazuhiro MARUYAMA,et.al: "Mechanism of the Grignard Reaction." J.Phys.Org.Chem.2. 205-213 (1989)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Hiroshi,YAMATAKA,et.al.: "Electron Transfer in the Reaction of Benzaldehyde with a Nonstabilized Ylide." Tetrahedron Letters. 7178 (1989)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] H.YAMAMOTO,et.al.et.al.: "Ultraviolet Photoelectron Spectroscopy of Perylene Anion in Csーperylene Solid." Mol.Cryst.Letters. 6. 171-183 (1990)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Y.YAMAMOTO,et.al.: "Reversible Bond Switch with Participation of Hypervalent Sulfurane in a Thiadiazole Ring System and Its Kinetic Study in a Protonated System." Bull,Chem.Soc.Jpn.62. 479-484 (1989)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Mizue FUJIO,et.al: "Substituent Effects on Solvolysis of Benzyl Tosylates." J.Phys.Org.Chem. 3. (1990)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] T.MENO,et.al: "Conformational Analysis of[3.3.3](1,3,5)Cyclophane Systems." Can.J.Chem. (1990)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] T.KITAMURA,et.al.: "Electrophilic Addition to oーArylーSubstituted Phenylalkynes.A Highly Selective Cyclization Controlled by Heteroatom." Tetrahedron Letters. 7745 (1989)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Tsutomu ASANO,et.al.: "Mechanism of Geometrical Isomerization about the CarbonーNitrogen Double Bond." J.Am.Chem.Soc.112. (1990)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Kaoru NAKAMURA,et.al: "Stereochemical Control in Microbial Reduction.12.(S)ー4ーNitroー2ーbutanol as a Source to Synthesize Natural Products." Bull.Chem.Soc.Jpn.63. 91-96 (1990)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Tadashi OKUYAMA,et.al.: "Mechanism of SecondーOrder Buffer Catalysis in the Hydrolysis of Methoxymethyl Banzenesulfenate." Chem.Lett.273-276 (1990)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Noboru ONO,et.al.: "Porphyrin Synthesis from Nitrocompounds." Tetrahedron. (1990)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Masaaki MISHIMA,et.al.: "Gas Phase Substituent Effects.Stabilities of 1ーArylー2,2,2ーtrifluoroethyl Cations." Tetrahedron Lett.685-688 (1990)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Hirochika SAKURAGI,et.al.: "Photochemical and Photophysical Behavior of p-Methoxyphenyl-alkenyl Phenanthrenecarboxylates.II.Kinetic Investigation of Intramolecular Cycloaddition." Bull.Chem.Soc.Jpn.63. 1058 (1990)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Jun-ichi HAYAMI, et.al.: "An Enatioselective Role of a Ternary Complex in the Asymmetric "Hydride" Transfer Reaction between NAD(P)H Model Compound and 5-Deazaflavin Possessing Planar Chirality." Tetrahedron Letters. 0000. (1990)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Shinya NISHIDA, et.al.: "Reactions of Some Cyclopropanes activated by a Spiro-Linked Fluorene. Importance of Electronic Matching of a Reacting Partner in Thermal Cycloaddition with TCNE and Ring-Opening Dehydrogenation with DDQ." J. Org. Chem.54. 3859-3868 (1989)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Mitsuo KIRA, Hideki SAKURAI, et.al.: "Highly Stereoselective Allylation of Aldehydes with Pentacoordinate Allyl-Silicates in Hydroxylic Media. Discrimination between Linear and Alpha-branched Alkanols." J. Am. Chem. Soc., 112, 257 (1989).

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Naoki INAMOTO, et.al.: "Relationship between Substituent Electronegativity and Field Parameter in the Aliphatic Series, Introduction of Charge Separation Parameter ( )." J. Phys. Org. Chem., 3, 2 (1990).

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Hiizu IWAMURA, et.al.: "Magnetic Coupling of Two Triplet Phenylnitrene Units Joined through an Acetylenic or Diacetylenic Linkage." Mol. Cryst. Liq. Cryst., 176, 33-48(1989).

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Hideyuki MATSUMOTO, et.al.: "Photolysis of Cyclotetrasilanes, a Remarkable Dependenace on Molecular Structure." J. Chem. Soc. Faraday Trans. I, 85, 2369-2379 (1989).

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Yasunori HASE, Minoru HIROTA, et.al.: "How to Determine the Force Constants of MM2 Force Field in a Consistent Way?" Chemistry Letters, 1507-1510 (1989).

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Yoshiaki HORIGUCHI, Isao KUWAJIMA, et.al.: "Does Me_3SiCl Activate Conjugate Addition of Copper Reagents as a Lewis Acid?" Tetrahedron Lett., 7087(1989).

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Nobuaki KOGA, Keiji MOROKUMA: "Ab Initio Molecular Orbital Studies of Intermediates and Transition States of Organometallic Elementary Reactions and Homogeneous Catalytic Cycles." Topics in Physical Organometallic Chemistry, 3, 1(1989).

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] M. KITAMURA, Ryo-ji NOYORI, et.al.: "Enantioselective Addition of Dialkylzincs to Aldehydes Promoted by Chiral Amino Alcohols. Mechanism and Nonlinear Effect." J. Am. Chem. Soc., 111, 4028(1989).

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Kaoru NAKAMURA, Takashi ANDO, et.al.: "Determination of the Configuration of Diastereomers of 2-Alkyl-3-hydroxybutanoates with Gas Chromatography." Bull. Chem. Soc. Jpn., 63, 298-300 (1990).

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Kazuhiro MARUYAMA et.al.: "Mechanism of the Grignard Reaction." J. Phys. Org. Chem., 2, 205-213(1989).

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Hiroshi YAMATAKA, Terukiyo HANAFUSA, et.al.: "Electron Transfer in the Reaction of Benzaldehyde with a Nonstabilized Ylide." Tetrahedron Lett., 7187 (1989).

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] H. YAMAMOTO, Kichisuke NISHIMOTO, et.al.: "Ultraviolet Photoelectron Spectroscopy of Perylene Anion in Cs-perylene Solid" Mol. Cryst. Letters, 6, 171-183 (1990).

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Y. YAMAMOTO, Kin-ya AKIBA: "Reversible Bond Switch with Participation of Hypervalent Sulfurane in a Thiadiazole Ring System and Its Kinetic Study in a Protonated System." Bull. Chem. Soc. Jpn., 62, 479-484 (1989).

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Mizue FUJIO, Yuho TSUNO, et.al.: "Substituent Effects on Solvolysis of Benzyl Tosylates." J. Phy. Org. Chem., 3, 0000 (1990).

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] T. MENO, Takahiko INAZU, et.al.: "Conformational Analysis of [3.3.3](1,3,5)Cyclophane Systems." Can. J. Chem., in press. (1990)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] T. KITAMURA, Hiroshi TANIGUCAHI, et.al.: "Electrophilic Addition to o-Aryl-Substituted Phenylalkynes. A Highly Selective Cyclization Controlled by Heteroatom." Tetrahedron Lett., 7745 (1989).

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Tsutomu ASANO, et.al.: "Mechanism of Geometrical Isomerization about the Carbon-Nitrogen Double Bond." J. Am. Chem. Soc., 112, 0000 (1990).

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Kaoru NAKAMURA, Atuyoshi OHNO, et.al.: "Stereochemical Control in Microbial Reduction. 12. (S)-4-Nitro-2-butanol as a Source to Synthesize Natural Products." Bull. Chem. Soc. Jpn., 63, 91-96 (1990).

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Tadashi OKUYAMA, et.al.: "Mechanism of Second-Order Buffer Catalysis in the Hydrolysis of Methoxymethyl Benzenesulfenate." Chem. Lett., 273-276 (1990).

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Noboru ONO: "Porphyrin Synthesis from Nitrocompounds." Tetrahedron, in press. (1990)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Masaaki MISHIMA, et.al.: "Gas Phase Substituent Effects. Stabilities of 1-Aryl-2,2,2-trifluoroethyl Cations." Tetrahedron Lett., 685-688 (1990).

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Hirochika SAKURAGI, et.al.: "Photochemical and Photophysical Behavior of p-Methoxyphenylalkenyl Phenanthrenecarboxylates. II. Kinetic Investigation of Intramolecular Cycloaddition." Bull. Chem. Soc. Jpn., 63, 1058 (1990).

    • Description
      「研究成果報告書概要(欧文)」より

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Published: 1993-03-26  

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