Address
Mizuno Laboratory, Department of Applied Chemistry, Graduate School of Engineering,
Osaka Prefecture University, 1-1 Gakuen-cho, Naka-ku, Sakai, Osaka 599-8531, Japan.
Tel: +81-72-254-9289 Fax: +81-72-254-9289
Staffs
Professor Kazuhiko Mizuno
Associate Professor Hiroshi Ikeda
Assistant Professor Hajime Maeda
Secretary Kayo Hirao
Students
D3 Teruyo Ikeda
D1 Maki Ohashi
M2 Masaru Inagaki
M2 Kenji Kawabata
M2 Azasa Sakai
M2 Yasuaki Nanai
M2 Hidenori Wada
M1 Akifumi Kawabe
M1 Takahiro Kanei
M1 Yasushi Fujimoto
M1 Shoji Matsuda
M1 Keita Minamida
M1 Kayo Yamamoto
B4 Yusuke Kano
B4 Nao Kishigami
B4 Keisuke Nakatani
B4 Naoki Negoro
B4 Takayuki Fujii
B4 Yasushi Matsui
Research Interests
Organic Photochemistry
Electron-Transfer Chemistry
Synthetic Chemistry
Organometallic Chemistry
Heteroatom Chemistry
Recent Publications
¡The Facile Generation of a Tetramethyleneethane Type Radical Cation and Biradical Utilizing a 3,4-Di(Éø-styryl)furan and a Photoinduced ET and Back ET Sequence"¡Intramolecular 9-Membered Hydrogen Bonding of 2-Arylmethylphenols Having Carbonyl Groups at 2Õ-Position, Yoshimi, Y.; Maeda, H.; Hatanaka, M.; Mizuno, K. Tetrahedron, 2004, 60(42), 9425-9431.
¡Diastereoselective Protonation on Radical Anions of Electron-Deficient Alkenes via Photoinduced Electron Transfer, Hayamizu, T.; Maeda, H.; Mizuno, K. J. Org. Chem. 2004, 69, 4997-5004.
¡Diastereoselectivity in (2ƒÎ+2ƒÎ) Photocycloaddition of Cholesteryl Cinnamate to Methyl 9-Phenanthrenecarboxylate: Control of the Stereoselectivity in Liquid Crystalline Phase, Maeda, H.; Horiuchi, A.; Koshio, N.; Mizuno, K. Chem. Lett. 2004, 33(8), 966-967.
¡Synthesis of Vinylidenecyclopropanes and Their Reactions, H. Maeda and K. Mizuno, J. Synth. Org. Chem. Jpn., 2004, 62(10), 1014-1025.
¡Photochemistry of Vinylidenecyclopropanes, K. Mizuno and H. Maeda, In CRC Handbook of Photochemistry and Photobiology Vol.2; Horspool, W. M. Ed.; CRC Press, Inc., 2004, 31/1-31/12.
¡Synthesis of 3,3,6,6-Tetraaryl-1,2-Dioxanes via TiO2-Catalyzed Photooxygenation of 1,1-Diarylethenes in the Presence of Mg(ClO4)2, Maeda, H.; Miyamoto, H.; Mizuno, K. Chem. Lett. 2004, 33(4), 462-463.
¡Reaction of Tetraazathiapentalene and Tetradiazolopyrimidine Derivatives with Heterocumulenes: Cycloaddition and Elimination Reactions via Hypervalent Sulfur Intermediates, N. Matsumura, A. Ito, M. Tomura, Y. Okumura, and K. Mizuno, J. Heterocyclic Chem., 2004, 41, 99-102.
¡Intramolecular (2ƒÎ+2ƒÎ) Photocycloaddition of Styrenes Tethered by Siloxanes, Maeda, H.; Yagi, H.; Mizuno, K. Chem. Lett.2004, 33(4), 388-389.
¡C1-C2 Bond Cleavage in Vinylidenecyclopropanes: Theoretical Density Functional Study, N. U. Zhanpeisov, K. Mizuno, M. Anpo, and J. Leszczynski, Int. J. Quantum Chem., 96, 343 (2004).
¡Photoaddition of Thiocarboxylic Acids to 2,3-Diallyltetraazathiapentalenes, N. Matsumura, O. Mori, T. Takeguchi, Y. Okumura, K. Mizuno, J. Heterocyclic Chem., 2004, 41, 1-2.
¡Formation and Cycloreversion of 2-Silacyclobuta[2.3]cyclophanes via
Photoinduced Electron Transfer, Mizuno, K.; Nakanishi, K.; Otsuji, Y.;
Hayamizu, T.; Maeda, H.; Adachi, T.; Ishida, A.; Takamuku, S. J.
Photoscience.
2003, 10(1), 121-126.
¡Synthesis and Dual Binding Character of Novel Cyclic Thiourea
Derivatives,
Okumura, Y.; Murakami, S.; Maeda, H.; Matsumura, N.; Mizuno, K.
Tetrahedron Lett. 2003, 44(44), 8183-8185.
¡Enhancement effect of Mg(ClO4)2 on TiO2-catalyzed photooxygenation
of 1,2-diarylcyclopropanes, Maeda, H.; Nakagawa, H.; Mizuno, K.
Photochem. Photobiol. Sci. 2003, 2(11), 1056-1058.
¡Bismuth-Catalyzed Allylation of Aldehydes and Ketones with Allyl
Bromides
in Water under Ultrasonic Wave Irradiation, N. Matsumura, T. Doi, K.
Mishima, Y. Kitagawa, Y. Okumura, and K. Mizuno, ITE Lett., on Batt.,
New Tech. & Med., 4, 473-477 (2003).
¡Cyclopropanation of Vinylidenecyclopropanes. Synthesis of
1-(Dihalomethylene)spiropentanes,
H. Maeda, T. Hirai, A. Sugimoto, and K. Mizuno, J.
Org. Chem., 68, 7700-7706 (2003).
¡Regioselective Photoaddition of Alcohols to 1,2,3-Butatriene
Derivatives
via Photoinduced Electron Transfer, H. Maeda, S. Nishioka, and K.
Mizuno,
Tetrahedron Lett., 44, 6601-6603 (2003).
¡Regio- and stereoselective functionailization of electron-deficient
alkenes by use of organosilicon compounds via photoinduced electron
transfer,
K.
Mizuno, T. Hayamizu, and H. Maeda, Pure Appl. Chem., 75, 1049-1054
(2003).
¡Photoinduced Electron Transfer Reactions of Organosilicon
Compounds,
T. Tamai, T. Hayamizu and K. Mizuno, Handbook of Photochemistry and
Photobiology, ed. by H. S. Nalwa, American Scientific Publishers, Vol.
1, 125-156 (2003).
¡Photochemical Polar Addition, M. Yasuda and K. Mizuno, Handbook of
Photochemistry and Photobiology, ed. by H. S. Nalwa, American
Scientific
Publishers, Vol. 2, 393-434 (2003).
¡Cyclopropenethione derivatives as reactive intermediate in organic
synthesis, N. Matsumura, Y. Okumura, Y. Yagyu, and K. Mizuno, Recent
Res.
Devel. Organic. Chem., 6, 709-745 (2002).
¡Synthesis of Feruloyl myo-inositol Derivatives and Their Inhibitory
Effects on Phorbol Ester-Induced Superoxide Generation and Epstein-Barr
Virus
Activation, A. Hosoda, E. Nomura, A. Murakami, K. Koshimizu, H.
Ohigashi,
K. Mizuno, and H. Taniguchi, Bioorg. & Med. Chem., 10, 1855-1863
(2002).
¡Thermal Instability of
5-(9-Anthrylmethyl)-10-methyl-5,10-dihydrophenazine.
A Quantum Chemical DFT Study, N. U. Zhanpeisov, A. Sugimoto, K.
Mizuno, M. Anpo, and J. Leszczynsky, J. Mol. Struc. (Theochem), 592
(No. 1-3), 149-153 (2002).
¡Synthesis and Properties of Novel Macrocyclic Compounds Bearing
Thiourea
Moieties by use of Chemical Feature of Hypervalent Sulfur, N.
Matsumura, T. Konishi, H. Hayashi, M. Yasui, F. Iwasaki, and K. Mizuno,
J. Heterocyclic Chem., 39, 189-202 (2002).
¡cis-trans Photoisomerization of Bicyclic
Diphenylvinylidenecyclopropanes,
H. Maeda, Z. Li, T. Hirai, and K. Mizuno, ITE Letters on Batteries, New
Technologies & Medicine, 3, 485-488 (2002).
¡A Novel Photoreaction of 1,2-Diarylcyclopropane with
9-Cyanophenanthrene:
The Formation of (3+2) Photocycloadducts, H. Maeda, Y. Miyata, and
K. Mizuno, Tetrahedron Lett., 43, 1481-1486 (2002).
¡Photoinduced Electron Transfer Reaction of Tetraazathiapentalenes
with Trialkylamines, H. Hayashi, N. Matsumura, and K. Mizuno, Chem.
Lett.,
2002, 510-511.
¡Synthesis of Ferulic Acid Derivatives and Their Suppressive Effects
on Cyclooxygenase-2 Promoter Activity, A. Hosoda, Y. Ozaki, A.
Kashiwada,
M.
Mutoh, K. Wakabayashi, K. Mizuno, E. Nomura, and H. Taniguchi, Bioorg.
& Med. Chem., 10, 1189-1196 (2002).
¡UV Absorption and Fluorescence Properties of Pyrene Derivatives Having Trimethylsilyl, Trimethylgermyl, and Trimethylstannyl Groups, H. Maeda, Y. Inoue, H. Ishida, K. Mizuno, Chem. Lett., 2001, 1224-1225.
¡Preparation of (})-1,6-Di-O-Feruloyl-myo-inositol Derivative: An Efficient Method for Introduction of Ferulic Acid to 1,6-Vicinal Hydroxyl Groups of myo-Inositol, A. Hosoda, E. Nomura, K. Mizuno, and H. Taniguchi, J. Org. Chem., 2001, 66, 7199-7201.
¡Facile Preparation of Ethyl 3-(4-Geranyloxy-3-methoxyphenyl)-2-propenoate (EGMP) and Related Compounds: For the Practical Use of EGMP as a Cancer Chemoprevantive agent, A. Hosoda, Y. Miyake, E. Nomura, K. Mizuno, and H. Taniguchi, ITE Lett. Batt. New Tech. Med., 2, 659-662 (2001).
¡Synthesis and Properties of Novel Macrocyclic Compounds Bearing Thiourea Moieties by Use of Chemical Feature of Hypervalent Sulfur, N. Matsumura, T. Konishi, H. Hayashi, M. Yasui, F. Iwasaki, and K. Mizuno, J. Heterocycl. Chem., 39, 189-202 (2002).
¡Intramolecular (4p+4p) photocycloaddition via naphthalene-furan exciplex, K. Chiyonobu, G. Konishi, Y. Inoue, and K. Mizuno, J. Chem. Res. (S), 2001, 135-137.
¡Site-selective Intramolecular Photocycloaddition of 2-Alkenyl-substituted 1-Cyanonaphthalenes Depending on Additives, Solvents, and Substituents, Y. Yoshimi, S. Konishi, H. Maeda, K. Mizuno, Synthesis, 1197-1202 (2001).
¡Site-selective Intramolecular (2p+2p) Photocycloaddition of trans-2-Butenyl 1-Cyano-2-naphthylmethyl Ether Depending on the Polarity of Solvent, Y. Yoshimi, S. Konishi, H. Maeda, K. Mizuno, Tetrahedron Lett., 42, 3475-3477 (2001).
¡A Novel (3+2) Photocycloaddition of Electron-Deficient Alkenes to Diarylvinylidenecyclopropanes: Regioselective Formation of Vinylidenecyclopentanes, K. Mizuno, H. Sugita, T. Hirai, H. Maeda, Y. Otsuji, M. Yasuda, M. Hashiguchi, and K. Shima, Tetrahedron Lett., 42, 3363-3366 (2001).
¡Photoallylation and Photoreduction of Cyclohexylidenepropanedinitrile by Use of Allyltrimethylsilane via Photoinduced Electron Transfer: Control of the Product Ratio Depending on Additives, T. Hayamizu, M. Ikeda, H. Maeda, and K. Mizuno, Org. Lett., 3, 1277-1280 (2001).
¡Highly Stereoselective Carbon-Functionalization of Electron-Deficient Arylalkenes by Use of Organosilicon Compounds via Photoinduced Electron Transfer, T. Hayamizu, H. Maeda, M. Ikeda, and K. Mizuno, Tetrahedron Lett., 42, 2361-2364 (2001).
¡Direct Observation of 1-Methoxycarbonyl-2-Naphthylmethyl Radical via Photo-Claisen Type Rearrangement, Y. Yoshimi, K. Mizuno, H. Maeda, N. Ichinose, T. Tanaka, and S. Kawanishi, Chem. Lett., 2001, 252-253.
¡A Novel Nine-Membered Intramolecular Hydrogen Bonding in Methyl Naphthoate Bearing Phenol Moiety, Y. Yoshimi, H. Maeda, A. Sugimoto, and K. Mizuno, Tetrahedron Lett., 42, 2341-2343 (2001).
¡Photorearrangement of Vinylidenecyclopropanes to 1,2,3-Butatriene Derivatives, K. Mizuno, H. Maeda, H. Sugita, S. Nishioka, T. Hirai, and A. Sugimoto, Org. Lett., 3, 581-584 (2001).
¡A novel cis-trans photoisomerization of vinylidenecyclopropanes via an electron transfer chain process, K. Mizuno, K. Nire, H. Sugita, and H. Maeda, Tetrahedron Lett., 42, 2689-2692 (2001).
¡Photocycloaddition and Photoaddition Reactions of Aromatic Compounds, K. Mizuno, H. Maeda, A. Sugimoto, and K. Chiyonobu, In Molecular and Supramolecular Photochemistry Vol. 8 Understanding and Manipulating Excited-State Processes; Ramamurthy, V., Schanze, K. S. Eds.; Marcel Dekker, Inc.: New York; 2001, pp 127-241.
¡Au/Poly(3-methylthiophene)/10-(p-nitrobenzyl)-2-(10H)-phenazinone/Al Organic Hetero-junction Photovoltaic Device, T. Mikayama, H. Matsuoka, M. Ara, K. Uehara, A. Sugimoto, and K. Mizuno, Solar Energy Materials & Solar Cells, 65, 133-139 (2001).
¡Nanometre-Scale Photoelectric Characteristics of a Molecular Device
Monolayer
T. Mikayama, M. Ara, K. Uehara, A. Sugimoto, K. Mizuno and N. Inoue
Phys. Chem. Chem. Phys., 3, 3459-3462 (2001).
¡Stereoselective Photocycloaddition of Alkenes to Naphthalene Rings Assisted by Hydrogen Bonding, A. Yokoyama and K. Mizuno, Org. Lett., 2, 3457-3459 (2000).
¡Stereospecific (2p+2p) Photocycloaddition of Arylalkenes to Pyrene via Exciplex: Formation of 1:1- and 2:1-Cycloadducts, K. Mizuno, H. Maeda, Y. Inoue, A. Sugimoto, L. P. Vo, and R. A. Caldwell, Tetrahedron Lett., 41, 4913-4916 (2000).
¡A Novel Cis-Trans Photoisomerization of Vinylidenecyclopropanes via Excited Singlet and Triplet States, K. Mizuno, H. Sugita, T. Hirai, and H. Maeda, Chem. Lett., 2000, 1144-1145.
¡A New Method for the Generation of o-Quinodimethane by Anodic Oxidation of o-Bis(trimethylstannylmethyl)benzene, Y. Ishii, Y. Inoue, H. Maeda, and K. Mizuno, ITE Letters on Batteries, New Technologies & Medicine, 1, 404-407 (2000).
¡Synthesis and Photochemical Properties of 2,2'-Silaspirobiindan and Related Compounds, Y. Inoue, A. Sugimoto, and K. Mizuno, J. Chem. Res. (S), 2000, 528-529.
¡Photochemical Oxygenation and Cross-Linking of Poly(4-trimethylsilylmethylstyrene) Thin Film by UV Irradiation, T. Tamai, N. Ichinose, S. Kawanishi, and K. Mizuno, Macromolecules, 33, 2881-2886 (2000).
¡Synthesis of Feruloyl-myo-inositols and their Inhibitory Effects on Superoxide Generation, A. Hosoda, E. Nomura, A. Murakami, K. Koshimizu, H. Ohigashi, K. Mizuno, and H. Taniguchi, Bioorg. Med.Chem. Lett., 10, 1439-1442 (2000).
¡One-Pot Synthesis of N-Heterocyclic Compounds from Cyclopropenethione Derivatives, N. Matsumura, Y. Yagyu, M. Ito, T. Adachi, and K. Mizuno, J. Org. Chem., 65, 3341-3345 (2000).
¡Synthesis of Novel Macrocyclic Compounds Utilizing Characteristic Bonding Properties of Hypervalent Sulfur, N. Matsumura, T. Konishi, H. Hayashi, M. Yasui, F. Iwasaki, and K. Mizuno, Heterocycles, 53, 1239-1245 (2000).
¡Site-Selective and Stereoselective Intramolecular (2p+2p) Photocycloaddition of Arylalkenes to Pyrene and Its Photocycloreversion, H. Maeda, A. Sugimoto, and K. Mizuno, Org. Lett., 2, 3305-3308 (2000).
¡Stereoselective (2p+2p) Photocycloaddition of Arylalkenes to Chrysene, H. Maeda, S. Waseda, and K. Mizuno, Chem. Lett., 2000, 1238-1239.
¡Synthesis and Antitumor Activities of Water-Soluble Benzoylphenylureas, H. Okada, M. Kato, T. Koyanagi, and K. Mizuno, Chem. Pharm. Bull., 47, 430-433 (1999).
¡Thermally Unstable 5-(9-Anthrylmethyl)-10-methyl-5,10-dihydrophenazine, A. Sugimoto, K. Matsumoto, H. Maruyama, K. Mizuno, and K. Uehara, J. Chem. Res.(S), 1999, 72-73; J. Chem. Res.(M), 1999, 601-697, 701-727.
¡Successive Electron Transfer Reaction of Lithium Salt of Methyl-5,10-dihydrophenazine Anion with 4-Nitrophenethyl Bromide via 4-Nitrostyrene, A. Sugimoto, H. Maruyama, W. Takahashi, K. Mizuno, K. Uehara, and T. Adac hi, J. Heterocyclic Chem., 36, 849-856 (1999).
¡Hydrobromic Acid-Dimethyl Sulfoxide Reagent for Dealkylation of 5,10-Dialkyl-5,10-dihydrophenazines: Synthesis of 10-Alkyl-2(10H)-phenazines, A. Sugimoto, Y. Yoshino, R. Watanabe, K. Mizuno, K. Uehara, J. Heterocyclic Chem., 36, 1057-1064 (1999).
¡Photoinduced Electron Transfer Reactions of Organosilicon Compounds, K. Mizuno, T. Tamai, A. Sugimoto, and H. Maeda, in Advances in Electron Transfer Chemistry VI, ed by P. S. Mariano, Jay Press, pp 131-165 (1999).
¡Nanometer-scale Unimonolayer Device Properties of High-quality Monolayer Film, T. Mikayama, H. Matsuoka, K. Uehara, A. Sugimoto, K. Mizuno, and N. Inoue, Denkigakkaironbunshi A, 118-A, 1435-1439 (1998).
¡Photochemical C-C Bond Cleavage of 1,2-Diarylcyclopropanes Bearing an Acetylphenyl Group. Generation and Observation of Triplet 1,3-Biradicals, N. Ichinose, K. Mizuno, Y. Otsuji. R. A. Caldwell, and A. M. Helms, J. Org. Chem., 63, 3176-3184 (1998).
¡Generation of Polyphenylene (PP) Radical Cations and Cosensitization of PP in the 9,10-Dicyanoanthracene-Sensitized Photochemical Chain Reactions of 1,2-Bis(4-methoxyphenyl)cyclopropane, T. Tamai, N. Ichinose, T. Tanaka, T. Sasuga, I. Hashida, and K. Mizuno, J. Org. Chem., 63, 3204-3212 (1998).
¡Synthesis and Reactivity of New 1,4-Bis(alkylthio)-3,6-diarylthieno [3,4-c]thiophene Derivatives, N. Matsumura, H. Tanaka, Y. Yagyu, K. Mizuno, H. Inoue, K. Takada, M. Yasui, and F. Iwasaki, J. Org. Chem., 63, 163-168 (1998).
¡A Novel Photorearrangement of Aryl Naphthylmethyl Ethers. Formation of Cyclohexa-2,4-dienone Derivatives, Y. Yoshimi, A. Sugimoto, H. Maeda, and K. Mizuno, Tetrahedron Lett., 39, 4683-4686 (1998).
¡Efficient One-Pot Preparation of 6-Methylsulfanyl-5-phenyl-2,3-dihydro-1H-pyrrolizine from 2-tert-Butylsulfanyl-3-phenyl- or pyrrolidine-1-yl-cyclopropenethiones, Y. Yagyu, M. Ito, N. Matsumura, H. Inoue, K. Mizuno, and T. Adachi, J. Chem. Soc., Perkin Commun., 1998, 1175-1177.
¡A Novel Intramolecular Photocyclization of 2-(4,5-Dimethyl-2-oxa-4-hexenyl)-1-methoxycarbonylnaphthalene via 1,9-Hydrogen Abstraction, K. Mizuno, S. Konishi, Y. Yoshimi, and A. Sugimoto, J. Chem. Soc., Chem. Commun., 1998, 1659-1660.
¡Formation of 1,1,2,3,3-Pentakis(arylthio)-1-propenes from Tris(arylthio)cyclopropenyl Cations and Their Conversion into 1,1,2,5,6,6-Hexakis(arylthio)-(3E)-1,3,5-hexatriene, N. Matsumura, Y. Shimizu, Y. Yagyu, H. Inoue, K. Mizuno, and T. Adachi, Heteroatom. Chem., 9, 387-397 (1998).
¡Observation of Monolayers of a Long-chain Alkyl Dihydrophenazine Derivative for a Photoelectric Molecular Device by Atomic Force Microscopy, T. Mikayama, K. Uehara, A. Sugimoto, H. Maruyama, K. Mizuno, and N. Inoue, Mol. Cryst. Liq. Cryst., 315, 211-216 (1998).
¡Oxidative Dimerization of 1,1,2,3,3-Pentakis(arylthio)-1-propene. Formation of Hexakis(arylthio)-(3E)-1,3,5-hexatriene Derivatives, N. Matsumura, Y. Shimizu, Y. Yagyu, K. Mizuno, and T. Adachi, Sulfur Lett., 21, 69-74 (1998).
¡Electrospray Mass Analysis of Chemical Oxidation of 1,2-Diarylcyclopropanes by Cu(II) Salt, M. Okamoto, H. Doe, K. Mizuno, T. Fukuo, and R. Arakawa, J. Am. Soc. Mass Spectrom., 9, 966-969 (1998).
¡Formation and Reactivity of Radical Cations of Cyclopropane
Derivatives,
K. Mizuno, S. Nishioka, H. Maeda, and N. Ichinose, Novel Trends in
Electroorganic
Synthesis, ed by S. Torii, Springer, Tokyo, 37-38 (1998).