Summary of Research Project Results Under the JSPS FY2000
"Research for the future Program"



1.Research Institution@Tokyo Institute of Technology
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2.University-Industry Cooperative Research Committee@116th Committee on Chemistry Creating Organic Compounds with Novel Functions
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3.Term of Project@FY1996`FY2000
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4.Project Number@96R11601
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5.Title of Project@Creations of Organic Functional Materials and Development of Their Svnthetic Methods Based on Characteristics of Hetero-atoms

6.Projetct Leader
Name Institution,Department Title of Position
Takeshi Nakai Tokyo Institute of Technology, Graduate School of Science and Engineering Professor

7.Core Members

Names Institution,Department Title of Position
Shin Tsuge Nagoya University, Graduate School of Engineering Professor

8.Cooperating Researchers

Names Institution,Department Title of Position
Tamejiro Hiyama Kyoto University, Graduate School of Engineering Professor
Masanobu Hidai Science University of Tokyo, Faculty of Industrial Science and Technology Professor
Etsuo Niki Utsunomiya University, Faculty of Engineering Professor

9.Summary of Research Results

The summary of research results of this project is divided into the two topics: "Creation and Function Evaluation" of heteroatom-containing functional organic compounds and "Development of Synthetic Methods" thereof.
"Creation and Evaluation": The main results are: (a) Creation of hybrid cyclynes and their Ag+-induced transformations into perylenes (Yoshida), (b) Synthesis and properties of polysila-cage compounds containing three Si-Si linkages (Hiyama), (c) Development of high performance liquid crystals with hetero atoms (Dohgane), (d) Development of environmentally benign materials derived from amino acids (Yamaguchi), (e) Analysis of lipid peroxidation in cell membranes using a new fluorescent probe (Niki), (f) A chromatographic method for characterization of abnormal structures in polycarbonates (Tsuge), (g) Development of electrochemical array as an integrated multi-electrode DNA sensor (Takagi), (h) Development of imprinted polymer microchip for capillary electrochromatography (Hobo).
"Synthetic Method": The main results include: (i) Discovery of a novel 1,4-phenyl migration reaction and application to synthesis of optically active silanols (Nakai), (j) Development of propargylic substitution reactions catalyzed thiolate-bridged diruthenium complexes (Hidai), (k) Synthesis of (boryl) (silyl) iminomethanes via insertion of isonitriles into Si-Si bond and catalytic asymmetric reactions using new herical ligands (Ito), (l) Development of new ruthenium-catalyzed [2+2+1]-cycloadditions leading to heterocycles (Murai), (m) Studies on reactivity of pseudorotamers of phosphoranes and creation of 5-coordinate carbon compounds (Akiba).

10.Key Words

(1)Hetero AtomsA(2)Fanctional Organic MeterialA(3)Oganosilicon Compounds
(4)Liquid CrystalA(5)DNA sensorA(6)Catalytic reactions
(7)Asymmetric SynthesisA(8)ChromatographyA(9)Environmentally Denign Meterials

11.References

[Reference Articles]
Author Title of Article
M. Hidai Novel Propargylic Substitution Reactions Catalyzed by Thiolate-Bridged Diruthenium Complexes via Allenylidene Intermediates
Journal Volume Year Pages Concerned
J. Am. Chem. Soc. 112 2000 11018-11020

Author Title of Article
M. Hidai Protonation of Coordinated N2 on Tungsten with H2 Mediated by Sulfido-bridged Dinuclear Molybdenum Complexes
Journal Volume Year Pages Concerned
Inorg. Chem. 40 2001 578-580

Author Title of Article
Z. Yoshida Electrochemical Transformation of 4-Cyanocinnolines into 4(1H)-Cinnolones.
Journal Volume Year Pages Concerned
Tetrahedron Lett. 41 2000 7901-7904

Author Title of Article
Z. Yoshida A Simple Hybrid Cyclyne Consisting of 1, 3-Diethynylbenzene and Ether Unites: Synthesis and Novel Ag+-Incluced Cyclization Leading to the Perylene Skeleton Formation.
Journal Volume Year Pages Concerned
J. Am. Chem, Soc. 112 2000 7404-7405

Author Title of Article
S. Murai Carbonylative [5 + 1]Cycloaddition of Cyclopropyl Imines Catalyzed by Ruthenium Carbonyl Complex
Journal Volume Year Pages Concerned
J. Org. Chem. 65 2000 9230-9233

Author Title of Article
S. Murai Ru3(CO)12-Catalyzed Intermolecular Cyclocoupling of Ketones, Alkenes or Alkynes, and Carbon Monoxide. [2+2+1]Cycloaddition Strategy for the Synthesis of Functionalized ƒÁ-Butyrolactones
Journal Volume Year Pages Concerned
J. Am. Chem. Soc. 112 2000 12663-12674

Author Title of Article
S. Murai The Ru3(CO)12-Catalyzed Intermolecular [2+2+1] Cyclocoupling of Imines, Alkenes or Alkynes, and Carbon Monoxide: A New Synthesis of Functionalized ƒÁ-Lactames
Journal Volume Year Pages Concerned
Synthesis @ 2000 925-928

Author Title of Article
T. Hiyama Palladium-iminophosphine-catalyzed Alkynylstannylation of Alkynes
Journal Volume Year Pages Concerned
Organometallics 19 2000 561-5678

Author Title of Article
T. Hiyama Synthesis and Structures of Polysilacage Compounds Containing a Silicon-silicon Inter-element Linkage
Journal Volume Year Pages Concerned
J. Organomet. Chem 611 2000 12-19

Author Title of Article
T. Nakai A Novel Aryl Migration from Silicon to Carbon: An Efficient Approach to Asymmetric Synthesis of ƒ¿-Aryl ƒÀ-Hydroxy Cyclic Amines and Silanols
Journal Volume Year Pages Concerned
J. Am. Chem. Soc 112 2000 408-409

Author Title of Article
E. Niki Stability and Reactivity of Aryloxyl Radicals Derived from a Novel Antioxidant BO-653 and Related Compounds. Effects of Substituent and Side Chain in Solution and Membranes.
Journal Volume Year Pages Concerned
J. Am. Chem. Soc 112 2000 5438-5442

Author Title of Article
A. Yamaguchii Preparation and Application of Poly (amino acid) Derivatives
Journal Volume Year Pages Concerned
The 3rd International Forum on Chemistry of Functional Organic Chemicals (IFOC-3) @ 2000 53

Author Title of Article
A. Yakaguchi ŠÜƒwƒeƒŒ´ŽqŠÂ‹«“K‰žÞ—¿‚ÌŠJ”­
Journal Volume Year Pages Concerned
“ú–{›{pU‹»‰ï‘æ116ˆÏˆõ‰ï‹ÆÑ•ñ @ 2000 33-36

Author Title of Article
I. Dogane ƒwƒeƒŒ´Žq‚ð—L‚·‚鍂‹@”\‰t»Þ—¿‚ÌŠJ”­
Journal Volume Year Pages Concerned
“ú–{›{pU‹»‰ï‘æ116ˆÏˆõ‰ï‹ÆÑ•ñ @ 2000 29-32

Author Title of Article
Y. Ito Structral Modification of Living Polymers: Synthesis of Helical Block Copolymers from a Single Monomer via Palladium-Mediated Aromatizing Polymerization of 1, 2-Diisocyanobenzenes.
Journal Volume Year Pages Concerned
Macromolecules 33 2000 4034-4038

Author Title of Article
M. Takagi Electrochemical Detection of Base Pair Mutation
Journal Volume Year Pages Concerned
Chemistry Letters 10 2000 1038-1039

Author Title of Article
M. Takagi DNA Sensing on a DNA Probe-Modified Electrode Using Ferrocenylnaphthalene Diimide as the Electrochemically Active Ligand
Journal Volume Year Pages Concerned
Analytical Chemistry 72 2000 1334-1341

Author Title of Article
K. Akiba Synthesis of a Versatile Tridentate Anthracene Ligand and Application for the Synthesis of Hypervalent Pentacoordinate Boron Compound (10-B-5).
Journal Volume Year Pages Concerned
Angew. Chem. Int. Ed. 38 2000 4055-4058

Author Title of Article
K. Akiba Synthesis and X-ray Crystal Structures of Hypervalent Arsenic Compounds Bearing Arsenic- Iron Bonds.
Journal Volume Year Pages Concerned
Heteroatom Chem. 11 2000 42-47

Author Title of Article
S.Tsuge Discriminative Analysis of Eucalyptus Camadulensis Grown from Various Origins Based on Lignin
Journal Volume Year Pages Concerned
“ú–{›{pU‹»‰ï‘æ116ˆÏˆõ‰ï‹ÆÑ•ñ 57 2001 145-152

Author Title of Article
S. Tsuge Structural Characterization of Polyoxymethylenes by Matrix-Assisted Laser Desorption/Ionization-Mass Spectrometry
Journal Volume Year Pages Concerned
Macromolecules 15 2001 82-88

Author Title of Article
T. Hobo Fabrication of polyester microchannnels and their application to capillary electrophoresis
Journal Volume Year Pages Concerned
J. Chromatogr. A 907 2001 279-289

Author Title of Article
T. Hobo Photo-responsive Retention Behavior of Azobenzene-modified Cyclodextrin Stationary Phase in Micro-HPLC
Journal Volume Year Pages Concerned
Anal. Sci 17 2001 119-124

[Reference Books]
Author Title of Book
T. Hiyama Organofluorine Compounds: Chemistry and Applications
Publisher Year Pages
Springer 2000 272

Author Title of Book
E. Niki Asvances in DNA Damage and repair
Publisher Year Pages
Plenum Pub., New york 2000 451

Author Title of Book
T. Nakai Precision Polymers and Nano-organized Systems
Publisher Year Pages
Kodansha 2000 347

Author Title of Book
T. Nakai Catalytic Asymmetric Synthesis
Publisher Year Pages
Wiley-VCH 2000 620


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