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Satoshi Yokoshima, Tetsuji Kubo, Hidetoshi Tokuyama, Tohru Fukuyama
2002 Volume 31 Issue 2 Pages
122-123
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A novel oxidative transformation of α-aminonitriles to amides is reported. Oxidation of α-aminonitriles with peracid, followed by basic treatment affords, amides in good yields. A mechanistic aspect of this transformation is also discussed.
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Hiroyuki Kusama, Fumiyasu Shiozawa, Masahide Shido, Nobuharu Iwasawa
2002 Volume 31 Issue 2 Pages
124-125
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o-Quinodimethanes, generated by the Diels-Alder reactions of benzopyranylidenetungsten(0) complexes with electron-rich dienes, further undergo intramolecular cyclizations to afford novel polycyclic compounds.
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Yukihiko Hashimoto, Satoshi Kikuchi
2002 Volume 31 Issue 2 Pages
126-127
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The combination of (
o-tolyl)
3P/TiCl
4 effectively promoted the Reformatsky-type reaction of α–bromoketone or -thioester derivatives with various aldehydes, and the corresponding β–hydroxy carbonyl compounds were obtained in good yield with high diastereoselectivity.
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Kouji Kuramochi, Yuko Osada, Takeshi Kitahara
2002 Volume 31 Issue 2 Pages
128-129
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We report a facile method for preparing enamides, based on the Curtius rearrangement and acylation of alkenylcarbamate. Using this approach, a total synthesis of coscinamide B, a bis indolic enamide, was achieved.
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Takayuki Shioiri, Naoko Irako
2002 Volume 31 Issue 2 Pages
130-131
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The stereoselective intramolecular Michael ring closure of the dipeptide efficiently gives the piperazinone fragment of pseudotheonamide A
1, a serine protease inhibitor from the marine sponge
Theonella swinhoei.
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Asit K. Chandra, Tadafumi Uchimaru, Masaaki Sugie, Akira Sekiya
2002 Volume 31 Issue 2 Pages
132-133
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The rate constant for the hydrogen abstraction reaction between CF
2ClOCHO and OH radical has been calculated for the first time by using the modified ab initio G2(MP2) and standard transition state theories. The Arrhenius equation for the rate constant,
ktotal, within the temperature range of 250 K to 450 K is estimated to be 7.1×10
-13exp(-845/
T) cm
3 molecule
-1 s
-1.
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Shoji Matsumoto, Takuya Kishimoto, Katsuyuki Ogura
2002 Volume 31 Issue 2 Pages
134-135
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Reaction of 1-(1
H-3-indolyl)-4-(methylthio)-2-(
p-tolylsulfonyl)-1,3-butadienes (
1) with iodine was accompanied with an unusual 1,2-migration of the sulfonyl group to give an abnormal cyclization product (
3). This 1,2-migration reaction was brought about by the action of hydrogen polyiodides that are produced from excess I
2 and EtSH. It is noteworthy that the reaction of
1 with HI resulted in formation of a normal product (
2).
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Akihiro Orita, Lasheng Jiang, Madoka Tsuruta, Junzo Otera
2002 Volume 31 Issue 2 Pages
136-137
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Synthesis of cyclophanes having alternating arylene-ethynylene as well as-ethenylene arrays is described. It is disclosed that these compounds are chiral on the basis of X-ray analysis and fluxional in solution on the basis of NMR spectra.
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Kazushi Hosoi, Kyoko Nozaki, Tamejiro Hiyama
2002 Volume 31 Issue 2 Pages
138-139
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Introduction of a 2-thienyl group to the silicon atom of alkenylsilanes promoted the cross-coupling reaction with aryl halides mediated by tetrabutylammonium fluoride and a palladium catalyst. The reaction proceeded under extremely mild conditions to afford arylalkenes in high yields.
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Yasushi Imada, Katsuya Ueno, Koji Kutsuwa, Shun-Ichi Murahashi
2002 Volume 31 Issue 2 Pages
140-141
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Asymmetric alkylation of 2,3-alkadienyl phosphates with soft carbon nucleophiles proceeds efficiently in the presence of palladium complex catalyst bearing MeOBIPHEP or BINAP ligand to give optically active functionalized allenes up to 90% ee.
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Makoto Hojo, Kyosuke Sakata, Xiamuxikamaer Maimaiti, Junya Ueno, Hisas ...
2002 Volume 31 Issue 2 Pages
142-143
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Enolates generated from α-bromo esters by the reduction with “Bu
6CrLi
3” react with oxiranes to afford γ-hydroxy esters and β-hydroxy esters, depending on the Lewis acid used as a promoter.
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Masayuki Yoshida, Mitsuru Kitamura, Koichi Narasaka
2002 Volume 31 Issue 2 Pages
144-145
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3,4-Dihydro-2
H-pyrroles were synthesized from γ,δ-unsaturated ketone
O-acetyloximes by treatment with acetic acid and 1,4-cyclohexadiene in the presence of a catalytic amount of 1,5-naphthalenediol. During the cyclization,
syn-
anti isomerization of the
O-acetyloximes easily occured and so, both stereoisomers of oximes could be employed.
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Masaharu Nakamura, Naohiko Yoshikai, Eiichi Nakamura
2002 Volume 31 Issue 2 Pages
146-147
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Dipolar trimethylenemethane species, thermally generated from 2,2-dialkoxy-1-methylenecyclopropane, reacts with a dialkylzinc reagent to generate an allylic zinc reagent, which then reacts in situ with a carbonyl compound to give a hydroxy acetal product as the result of coupling of the three reactants.
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Goh Matsuo, Hitomi Kadohama, Tadashi Nakata
2002 Volume 31 Issue 2 Pages
148-149
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The highly stereoselective syntheses of 2,3-
trans-3-hydroxy-tetrahydropyran and oxepane were achieved by the SmI
2-induced reductive intramolecular cyclizations from acyclic compounds having an aldehyde and a β-alkoxyacrylate. The syntheses of tetrahydrofuran, oxocane, and oxocene were also accomplished.
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Shin-ichiro Shoda, Ryuko Izumi, Masako Suenaga, Kenji Saito, Masaya Fu ...
2002 Volume 31 Issue 2 Pages
150-151
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A potassium fluoride-promoted intramolecular cyclization reaction of 2-acetamido-2-deoxy-α-D-glucopyranosyl chloride took place smoothly, giving the corresponding 1,2-oxazoline derivative in good yield. Potassium fluoride behaves as a nucleophile for anomerization of the glycosyl chloride as well as an acid captor to scavenge the protonic acid liberated. This is an extremely practical method for preparation of sugar oxazoline derivatives with simple experimental procedures.
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Shigeru Yamago, Takeshi Yamada, Ryuji Nishimura, Hiroki Ito, Yosuke Mi ...
2002 Volume 31 Issue 2 Pages
152-153
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Stannyl ethers are prepared by triflic acid-catalyzed reaction of alcohols with tributylstannane or allyltributylstannane at room temperature. The stannyl ethers thus prepared can be successfully used for the β-bromogycoside-mediated glycosylation reactions.
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Toshiyuki Itoh, Eri Akasaki, Yoshihito Nishimura
2002 Volume 31 Issue 2 Pages
154-155
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Lipase-catalyzed transesterification was demonstrated using methyl esters as acyl donors under reduced pressure in an ionic liquid ([bmim]PF
6) solvent system. The transesterification of 5-phenyl-1-penten-3-ol took place smoothly under reduced pressure at 27 hPa at 40 °C when methyl phenylthioacetate was used as acyl donor in [bmim]PF
6, and we succeeded in obtaining the corresponding acylated compound in optically pure form; this makes it possible to use lipase repeatedly because there was no drop in the reaction rate despite three repetitions of the process.
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Keiichiro Kakimoto, Nobukatsu Nemoto, Fumio Sanda, Takeshi Endo
2002 Volume 31 Issue 2 Pages
156-157
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Six-membered cyclic thiocarbonate derivatives, 5,5-(bicyclo[2.2.1]hept-2-en-5,5-ylidene)-1,3-dioxane-2-thione (
1) and 5,5-(bicyclo[2.2.1]heptan-5,5-ylidene)-1,3-dioxane-2-thione (
2) underwent anionic ring-opening polymerization initiated by 1,8-diazabicyclo[5.4.0]-7-undecene (DBU) to afford polythiocarbonates accompanying 12.3 and 12.6% volume expansion, respectively.
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Ming Bao, Hiroyuki Nakamura, Akihiko Inoue, Yoshinori Yamamoto
2002 Volume 31 Issue 2 Pages
158-159
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The reaction of the allylic halides
5–
9 having an aldehyde or an imine moiety in the molecule with allyltributylstannane proceeded smoothly in the presence of Pd
2•dba
3•CHCl
3 (5 mol%) in DMF or THF, giving the corresponding heterocycles
10–
14 in good to high yields. The Stille coupling product was not obtained under these reaction conditions.
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Masatoshi Asami, Atsushi Seki
2002 Volume 31 Issue 2 Pages
160-161
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Polymer-bound lithium dialkylamides were prepared from the corresponding polymer-bound amines and butyllithium. The reagent was successfully employed as an
in situ regenerating agent of a chiral lithium amide in a catalytic enantioselective rearrangement of
meso-epoxides, and chiral allylic alcohols were obtained in up to 95% ee.
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Yoshinori Naruta, Masa-oki Goto, Toshifumi Tawara, Fumito Tani
2002 Volume 31 Issue 2 Pages
162-163
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An amphiphilic iron porphyrin having four hexadecanoic acid chains on each face of the porphyrin was prepared and the catalytic epoxidation of linolenic acid with the heme-casted bilayer membranes was achieved in high regioselectivity at the terminal double bond of the substrate. The orientation of the porphyrin ring in the membrane was determined to be parallel to the aqueous-bilayer interface by means of ESR.
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Isamu Shiina, Katsuhiko Konishi, Yu-suke Kuramoto
2002 Volume 31 Issue 2 Pages
164-165
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Various optically active secondary alcohols are obtained by asymmetric alkylation of aldehydes with diethylzinc by way of a new catalyst system, ((
R)-thiolan-2-yl)diphenylmethanol and several metal alkoxides. The transition states are also discussed in terms of experimental results and theoretical calculation.
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Makoto Onaka, Naoki Hashimoto, Ryota Yamasaki, Yasuyoshi Kitabata
2002 Volume 31 Issue 2 Pages
166-167
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Nanoporous aluminosilicate, Al-HMS with a high aluminum content, strong acidity, and nanoporosity was found to catalyze the Diels-Alder reaction of 1,3-dienes with methacrylate and acrylate, and turned out to be a green alternative to homogeneous acid catalysts.
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Itaru Sato, Shunji Osanai, Kousuke Kadowaki, Tadashi Sugiyama, Takanor ...
2002 Volume 31 Issue 2 Pages
168-169
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An atropisomeric hydrocarbon, (
R)-1,1′-binaphthyl, acts as a chiral initiator of asymmetric autocatalysis of pyrimidyl alkanol in the enantioselective addition of diisopropylzinc to pyrimidine-5-carbaldehyde to afford (
S)-5-pyrimidyl alkanol
2 with 96% ee. On the other hand, in the presence of (
S)-1,1′-binaphthyl, the reaction affords (
R)-
2 with 94% ee.
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Satoshi Kojima, Kazuhiro Kawaguchi, Shiro Matsukawa, Keiichiro Uchida, ...
2002 Volume 31 Issue 2 Pages
170-171
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Phosphoranes (10-P-5) bearing cyanomethyl, acetamide, and
N,
N-dimethylacetamide groups were examined for Wittig type reactions. All three reacted to give the corresponding olefins. The reaction of the cyanomethyl reagent with aldehydes gave α,β-unsaturated cyanides with high
Z-selectivity in the case of aliphatic aldehydes (
Z:
E=94:6 to 99:1). On the other hand, the reactions of the two amide reagents with aldehydes yielded α,β-unsaturated amides with high
Z-selectivity for both aromatic and aliphatic aldehydes (
Z:
E=99:1 to >99:<1).
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Kazuhiko Takai, Yoshito Ikawa, Keijiro Ishii, Makoto Kumanda
2002 Volume 31 Issue 2 Pages
172-173
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Allylic gallium sesquibromides prepared by reduction of allylic bromides with gallium metal in the presence of a catalytic amount of indium, add to terminal alkynes with the aid of a tertiary amine to give 1,4-dienes.
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Masumi Asakawa, Taichi Ikeda, Nobuhiko Yui, Toshimi Shimizu
2002 Volume 31 Issue 2 Pages
174-175
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The porphyrin-stoppered rotaxane was prepared from dibenzo-24-crown-8 (DB24C8) and the secondary ammonium ion derivative end-capped by the axial coordination of rhodium(III) tetra-(3,5-di-
tert-butylphenyl) porphyrin [TBPP Rh(III) Cl]. This rotaxane molecule was designed aiming at the immobilization on a substrate and the analysis of the physicochemical properties as a single molecule.
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Yong Zhang, Ke Li Zhang, Man Ke Jia, Hao Tang, Ju Tang Sun, Liang Jie ...
2002 Volume 31 Issue 2 Pages
176-177
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A novel compound, a rare earth complex oxide SnEr
2O
4 was synthesized by the thermal decomposition of its oxalate precursor prepared by Rheological Phase Reaction Method. TG, IR, XRD and XPS were used to prove the formation of the compound SnEr
2O
4. The structure of SnEr
2O
4 was defined by Rietveld analysis. SnEr
2O
4 is cubic,
Pm3
m,
a=7.3735 Å,
V=400.88 Å
3,
Z=4,
Dx=8.573 g/cm
3,
Dm=8.2 g/cm
3.
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Zameer Shervani, Yutaka Ikushima
2002 Volume 31 Issue 2 Pages
178-179
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In situ UV-vis spectroscopy has been applied to study the hydrolysis of acetylsalicylic acid, as a model reaction, in sodium bis(2-ethylhexyl)sulfosuccinate (AOT)/supercritical ethane reverse micelles in the presence of imidazole as a catalyst. A 55-fold increase in the rate constant was observed in AOT/supercritical ethane micelles compared to the reaction carried out in aqueous buffer medium. The promotion of hydrolysis in the micelles as compared to aqueous solution has originated from compartmentalization of water-soluble reactant and the catalyst in the aqueous core of micelles.
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Takayuki Sumida, Yuji Wada, Takayuki Kitamura, Shozo Yanagida
2002 Volume 31 Issue 2 Pages
180-181
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Three-dimensional macroporous tungsten trioxide (WO
3) was electrochemically prepared by using the polystyrene opal as a template. The photonic stop band of the porous WO
3 film could be changed when the WO
3 was intercalated with lithium cation by the electrochemical method. The change of the stop band was attributed to the change of the refractive indices accompanied with the electrochromism of WO
3.
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Hidehiko Fujisawa, Teruaki Mukaiyama
2002 Volume 31 Issue 2 Pages
182-183
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A catalytic aldol reaction between trimethylsilyl enol ethers and aldehydes by using lithium diphenylamide, a Lewis base catalyst, in DMF or pyridine solvent proceeded smoothly to afford the corresponding aldols under mild conditions.
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Yoshihiko Tezuka, Yoshitaka Bando, Hitoshi Tanaka
2002 Volume 31 Issue 2 Pages
184-185
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Two kinds of dehydroalanine monomers,
N-isobutyryl dehydroalanine (iBDHA) and its methyl ester (iBDHAM), were synthesized and their homopolymers were prepared by free radical polymerization. While poly(iBDHA) did not show any phase transition in water, poly(iBDHAM) exhibited the lower critical solution temperature (LCST) at 19 °C to form colloidal dispersion of nanoparticles with 60 nm diameter above the LCST. This nanoparticle formation was thermoreversible.
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Akira Mori, Shin-ichi Yamamoto, Manabu Takemoto, Seiji Ujiie
2002 Volume 31 Issue 2 Pages
186-187
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Unsymmetrical bis(5-alkoxy-2-aminotroponato)coppers showed tilted smectic C and G/J phases due to the alignment of the outboard dipole moment. Furthermore, their
N,
N-dimethyl derivatives had nematic and smectic A phases with low transition temperatures due to the reduction of the lateral overlapping and the steric repulsion of the methyl groups.
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Jun-ichiro Setsune, Takashi Yamauchi, Sachiko Tanikawa
2002 Volume 31 Issue 2 Pages
188-189
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(η
4-1,5-Cyclooctadienyl)rhodium(I) complex with a bidentate
N21,
N22-bridged porphyrin ligand was prepared. The η
4-1,5-cyclooctadiene ligand was easily replaced by carbon monoxide to give the corresponding (dicarbonyl)rhodium(I) porphyrin. The structures of these two complexes were proven by X-ray crystallography.
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Akira Yamaguchi, Saulius Juodkazis, Shigeki Matsuo, Hiroaki Misawa
2002 Volume 31 Issue 2 Pages
190-191
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In this study, we demonstrate that the Au particle modified probe DNA monolayer can enhance the surface plasmon resonance (SPR) signal for measuring hybridization of unlabeled DNA molecules. The Au particles adsorbed on single stranded (ss)- and double stranded (ds)-DNA monolayers have different optical interaction with surface of Au thin film, and this difference induces the enhancement of the SPR signal.
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Kazuhide Mima, Takashi Ishihara, Saki Kuwahata, Tsutomu Konno, Hiroki ...
2002 Volume 31 Issue 2 Pages
192-193
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α-Bromo-α-fluoro-β-hydroxy esters, prepared as isomeric mixtures by the zinc-mediated coupling reaction of dibromo-fluoroacetate with aldehydes at -20 °C, were successively treated with trimethylaluminium at -15 °C for 0.5 h and with tributyltin hydride in the presence of a catalytic amount of triethylborane at -15 °C for 4 h or at -78 °C for 6 h to give preferentially the
threo-isomers of the corresponding α-fluoro-β-hydroxy esters in good yields.
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Yasuhiro Morisaki, Yoshiki Chujo
2002 Volume 31 Issue 2 Pages
194-195
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Novel through-space π-conjugated polymers having [2.2]paracyclophane and fluorene units were synthesized by Heck-Sonogashira coupling reaction. The polymers exhibited strong blue fluorescence in solution and in the solid state.
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Feng Wang, Yonghong Ni, Xuewu Ge, Zhicheng Zhang
2002 Volume 31 Issue 2 Pages
196-197
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The flake-like silver nanocrystals were prepared by γ-irradiation in the presence of an electric field. However, only spherical silver nanoparticles were obtained without the electric field.
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Daofeng Sun, Rong Cao, Yucang Liang, Maochun Hong
2002 Volume 31 Issue 2 Pages
198-199
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Self-assembly of dipotassium salt of piperazine-1,4-bis(2-ethanesulfonic acid) (K
2pesp) with AgNO
3 in H
2O/DMF gave rise to a novel three-dimensional sulphonate silver(I) complex, [Ag
2(μ
2-OH
2)(pesp)]
n (
1). Each silver(I) ion is coordinated by one nitrogen and two oxygen atoms from three pesp ligands and one oxygen atom from coordinated water molecule in a distorted tetrahedral geometry.
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Kazuo Shinozuka, Masaaki Onodera, Hiroshi Ikeda, Hiroaki Sawai
2002 Volume 31 Issue 2 Pages
200-201
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Novel oligodeoxyribonucleotides containing a C-2 branched polyamine-bearing deoxyinosine moiety at either inside-region or the 5′-terminus of the sequence exhibited enhanced nuclease resistant property. Among them, only the oligomers having the modified deoxyinosine residue at inside-region brought about duplex stabilizing effect upon mixing with the complements.
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Olivier Vigneau, Catherine Pinel, Marc Lemaire
2002 Volume 31 Issue 2 Pages
202-203
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Competitive extraction of Gd/La, Gd/Nd, Gd/Eu, Gd/Lu and Am/Eu with a gadolinium-imprinted polymer leads to improvement of the selectivity compare to the corresponding blank material.
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Katsuaki Shimazu, Ryo Goto, Keijiro Tada
2002 Volume 31 Issue 2 Pages
204-205
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The tin-modified platinum and palladium-deposited gold (Sn/Pt and Sn/Pd/Au) electrodes have exhibited a higher electrocatalytic activity for the reduction of nitrate than any electrode so far reported in the literature. Ammonium ions were predominantly formed on Sn/Pt, while N
2O and/or N
2 were the most likely main products on Sn/Pd/Au.
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Zhi-Ze Ou, Jing-Rong Chen, Xue-Song Wang, Bao-Wen Zhang, Yi Cao
2002 Volume 31 Issue 2 Pages
206-207
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Cu
2+, Fe
2+ and Fe
3+ could chelate with cyclodextrin-modified hypocrellin (HBCD) efficiently and the UV-visible spectra of the resultant metal complexes red shifted by more than 40 nm. ESR study revealed that the hydroxyl radical was the main product during irradiation of these metal complexes because Cu
2+, Fe
2+ and Fe
3+ initiated the Fenton reaction. Also, these metal complexes photodamaged the calf thymus DNA in the liposome system 20 folds faster than that in the buffer solution due to the initiation of lipid peroxidation.
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M. Emran Quayum, Toshihiro Kondo, Satoshi Nihonyanagi, Dai Miyamoto, K ...
2002 Volume 31 Issue 2 Pages
208-209
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The formation of an octadecyl monolayer on a hydrogen terminated Si(111) surface in neat octadecene at 200 °C was followed by attenuated total reflectance Fourier transform infrared (ATR FT-IR) and sum frequency generation (SFG) spectroscopy and ellipsometry. Until ca. 60% of the monolayer was formed, the monolayer formation proceeded with simple first-order reaction kinetics and the monolayer was disordered. As the coverage steadily increased, the order of the monolayer became very high and the rate of the monolayer formation became significantly slower.
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Ejabul Mondal, Pankaj M. Bujar Barua, Gopal Bose, Abu T. Khan
2002 Volume 31 Issue 2 Pages
210-211
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Various thioglycosides
1 are smoothly hydrolyzed chemoselectively to the corresponding 1-hydroxy sugars
2 in good yields at 0–5 °C by employing (NH
4)
6Mo
7O
24·4H
2O-H
2O
2 or H
2MoO
4·H
2O-H
2O
2 to promote oxidation of ammonium bromide in the presence of perchloric acid in CH
2Cl
2-H
2O solvent system. Mild conditions, good yields, no side reactions such as bromination either at the anomeric position or double bond, and even oxidation at the sulfur are some of the major advantages.
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David Raju Burri, Ki-Won Jun, Young-Ho Kim, Ji Man Kim, Sang-Eon Park, ...
2002 Volume 31 Issue 2 Pages
212-213
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Cobalt(III) complex has been heterogenized onto a mesoporous material SBA-15 and successfully applied to the liquid phase oxidation of
p-xylene in spite of not using either a solvent or bromide ion.
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Shunai Che, Yasuhiro Sakamoto, Osamu Terasaki, Takashi Tatsumi
2002 Volume 31 Issue 2 Pages
214-215
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The 3d-cubic
Pm3-
n SBA-1 mesoporous silica synthesized under highly acidic conditions using cetyltrimethylammonium bromide exhibited a distinct octadecahedron crystal shape in contrast to the material synthesized in the presence of cetyltriethylammonium bromide under less acidic conditions, which showed a highly isotropic morphology with fifty-four or more crystal faces.
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Yoshimune Nonomura, Kenkou Kurita, Akio Kashimoto, Hajime Hotta, Yohei ...
2002 Volume 31 Issue 2 Pages
216-217
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Calcium lauroyl taurate (C
11H
23CONH(CH
2)
2SO
3·0.5Ca, CaLT) was synthesized, and the internal structure and tribology were studied. The powder of CaLT is a plate type crystal whose structure is lamellar at room temperature. When the powder is applied to an artificial skin, the frictional coefficient is lower than that for other solid lubricants. Such a high lubricity is caused by disintegration of the powder aggregates, cleavage of the lamellar layers, and deformation of the powder particles.
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Yoshinobu Saiki, Yuichi Ishikawa, Yutaka Amao
2002 Volume 31 Issue 2 Pages
218-219
Published: 2002
Released on J-STAGE: February 05, 2002
JOURNAL
RESTRICTED ACCESS
Photoinduced hydrogen production from sucrose as an electron-donating reagent has been investigated. When the sample solution containing sucrose, invertase, glucose dehydrogenase, nicotinamide adenine dinucreotide (NAD
+), zinc tetraphenylporphyrin tetrasulfonate (ZnTPPS), methylviologen and colloidal platinum was irradiated, continuous hydrogen production was observed.
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Hao Chen, Wei-Lin Dai, An-Ren Jiang, Jing-Fa Deng
2002 Volume 31 Issue 2 Pages
220-221
Published: 2002
Released on J-STAGE: February 05, 2002
JOURNAL
RESTRICTED ACCESS
The oxidative cleavage of cyclopentene to glutaraldehyde with aqueous H
2O
2 was performed over a peroxy-niobic acid catalyst with high yield (72%) and complete conversion of cyclopentene under mild reaction conditions. Peroxy-niobic acid has been shown as a “reaction-controlled phase-transfer” catalyst, which has the advantages of both homogeneous and heterogeneous catalysts.
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