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Kazuhiko Mizuno, Isao Nakanishi, Nobuyuki Ichinose, Yoshio Otsuji
1989 Volume 18 Issue 7 Pages
1095-1098
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The 9,10-dicyanoanthracene (DCA)-sensitized photoaddition of methanol to arylalkenes occurred both in benzene and acetonitrile to give the corresponding anti-Markownikoff type adducts. The efficiency of the photoreaction depended on the solvents and the structures of the substrates. The geminate radical ion pair in benzene and the solvent separated radical cation in acetonitrile were proposed as key intermediates. The stereochemical feature of the photoaddition of methanol to 1,2-dihydro-4-phenylnaphthalene was also described.
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Naoki Toshima, Ru-Jang Lin, Masao Kaneko
1989 Volume 18 Issue 7 Pages
1099-1102
Published: 1989
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The transient spectroscopic studies were carried out on a Prussian Blue (PB) membrane coated on an ITO electrode (5 cm × 1 cm), on which an electronic state gradient was realized. An isosbestic point was clearly observed in the trasient spectral changes when the PB was oxidized upon application of a potential from open-circuit to 1.5 V difference between the membrane terminals. The transient spectra observed on stepping back to open circuit showed three isosbestic points from the entirely oxidized state to the reduced states, to which a new electron transfer process is proposed.
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Norio Miura, Kuniaki Kanamaru, Youichi Shimizu, Noboru Yamazoe
1989 Volume 18 Issue 7 Pages
1103-1106
Published: 1989
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An amperometric proton-conductor sensor was newly developed for the selective detection of CO at room temperature by using a couple of Pt-loaded oxide (SnO
2 and WO
3) electrodes. The CO sensitivity of the sensor element was about 7 times higher than the H
2 sensitivity and the 90% response time was about 3 min. The selective detection of H
2 was possible when a Pt-black electrode was combined with a Pt-loaded WO
3 electrode.
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Hideki Kinoshita, Shingo Tanaka, Katsuhiko Inomata
1989 Volume 18 Issue 7 Pages
1107-1108
Published: 1989
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2-Methoxymethylpyrrole derivatives readily available from 2-methylthiomethylpyrroles were found to be readily cyclized to porphyrinogens with formic acid, and subsequent oxidation with O
2 affords the corresponding porphyrins in excellent yields.
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Kazutsugu Matsumoto, Hiromichi Ohta
1989 Volume 18 Issue 7 Pages
1109-1112
Published: 1989
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A new type of enzyme-mediated kinetic resolution has been developed. Enol esters, such as dl-3-acetoxy-1-
p-methoxy-benzyloxy-2-methoxymethoxy-3-pentene, were hydrolyzed by incubation with
Bacillus coagulans to afford optically pure enol esters, and the corresponding α-substituted ketones.
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Philippe Cotelle, Didier Barbry, Bruno Hasiak, Daniel Couturier
1989 Volume 18 Issue 7 Pages
1113-1114
Published: 1989
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Enamines are the thermal rearrangement products of (5
R*,6
R*)-6-dimethylamino-4-methylene-1-thiaspiro(4,5)-2-decene and (4,4)-2-nonene, and (5
R*,6
S*)-6-dimethylamino-1-methylene-2-thiaspiro(4,4)-3-nonene. The mechanism of formation of these compounds is discussed.
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Kiyoshi Tanaka, Takami Mori, Keiryo Mitsuhashi
1989 Volume 18 Issue 7 Pages
1115-1118
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Thermal ring transformation of 3-benzoylisoxazolidines gives 2-hydroxydihydrofurans together with α-benzoylenamines, the product ratio of both compounds depending on the 4- and 5-substituents of the isoxazolidine ring. The ring transformation is in contrast to the case of analogous 3-phenylisoxazolidines, resulting in 1,3-dipolar cycloreversion.
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Hsien-Chang Chang, Tomokazu Matsue, Isamu Uchida, Tetsuo Osa
1989 Volume 18 Issue 7 Pages
1119-1122
Published: 1989
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The bioelectrocatalytic reduction of NAD
+ to NADH on diaphorase immobilized electrodes was investigated using seven viologen derivatives with various side chains. The hydrophobic interaction between the enzyme and mediator has been shown to promote the reduction.
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Robert Chênevert, Daniel Chamberland
1989 Volume 18 Issue 7 Pages
1123-1124
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18-Crown-6 forms a stable 1:2 host–guest complex with chloral hydrate. This complex is not dissociated in non-polar solvents.
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Eisaku Nomura, Hisaji Taniguchi, Sadao Tamura
1989 Volume 18 Issue 7 Pages
1125-1126
Published: 1989
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A calix[6]arene derivative containing azo groups was synthesized. The solvent extraction of metal picrates by this compound was selective for Ag
+, Hg
+, and Hg
2+
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Isao Shimizu, Hirotoshi Ishii, Atsuma Tasaka
1989 Volume 18 Issue 7 Pages
1127-1128
Published: 1989
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Distannoxane-catalyzed transesterification of ethyl 4,4,4-trifluoroacetoacetate with allylic alcohols gave the corresponding allylic esters, which were subjected to palladium-catalyzed decarboxylation-allylation to give trifluoromethyl ketones.
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Tsutomu Kamiyama, Masami Inoue, Saburo Enomoto
1989 Volume 18 Issue 7 Pages
1129-1130
Published: 1989
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The epoxidation of alkenes with H
2O
2 was carried out in the presence of molybdenum oxide(VI)–(Bu
3Sn)
2O in CHCl
3 at 25 °C. In the oxidation of cyclohexene, styrene, and α-pinene, the addition of amines was indispensable and the yields of oxides reached 87 to 57%.
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Takaji Fujiwara, Naoki Tanaka, Kensaku Hamada, Shoichi Kobayashi
1989 Volume 18 Issue 7 Pages
1131-1134
Published: 1989
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Cryatal and molecular structure of a branched α-cyclodextrin, 6-
O-α-D-grucopyranosyl α-cyclodextrin was studied by X-ray structure analysis. A branched grucopyranose moiety is included in the cavity of another α-cyclodextrin moiety from the side of its secondary hydroxyl groups.
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Yasufumi Tamai, Tomoyuki Nakano, Sinji Koike, Kan Kawahara, Sotaro Miy ...
1989 Volume 18 Issue 7 Pages
1135-1136
Published: 1989
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A lipase from pseudomonas was found to catalyze almost completely enantioselective hydrolysis of the valerate of racemic 1,1′-binaphthyl-2-ol (
1). The Prelog’s atrolactic acid synthesis by use of (a
R)-
1 induced
S-chirality with much lower levels of optical yields (3–17%) than that reported previously (85%).
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Katsuyoshi Hoshino, Seiichiro Yokoyama, Tetsuo Saji, Hiroshi Kokado
1989 Volume 18 Issue 7 Pages
1137-1140
Published: 1989
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Thin films of copper phthalocyanine and metal-free phthalocyanine were electrochemically prepared on an Al substrate from their aqueous surfactant solutions. Surface coverage of these pigments was investigated as a function of the amount of electricity. Characterization of the films were performed with SEM, IR, and visible absorption spectroscopies.
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Kyoko Takahashi, Makoto Shibagaki, Hideyuki Kuno, Hajime Matsushita
1989 Volume 18 Issue 7 Pages
1141-1144
Published: 1989
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The vapor-phase reduction of carboxylic acids with 2-propanol was found to proceed efficiently over hydrous zirconium(IV) oxide, and the corresponding alcohols were obtained in high yield. Esters were also reduced.
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Yasuhiko Shirota, Tomokazu Kobata, Naoki Noma
1989 Volume 18 Issue 7 Pages
1145-1148
Published: 1989
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A novel class of starburst molecules for making amorphous glassy organic materials, 4,4′,4″-tris(
N,
N-diphenylamino)triphenylamine (TDATA) and 4,4′,4″-tris[
N-(3-methylphenyl)-
N-phenylamino]triphenylamine (MTDATA), are synthesized and characterized. Their electrochemical and electronic properties as well as unique solid-state morphology are described.
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Keiji Yamamoto, Norio Yamamoto
1989 Volume 18 Issue 7 Pages
1149-1152
Published: 1989
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The autoxidation of the dialkylzinc well precedes the conjugate addition of this reagent to α,β-unsaturated ketones, which undergo nucleophilic epoxidation with the resulting alkylperoxozinc species.
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Satoshi Tachiyashiki, Kunihiko Mizumachi
1989 Volume 18 Issue 7 Pages
1153-1154
Published: 1989
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In the photosubstitution of [Ru(bpy)
3]
2+ in aqueous acidic (HX) solutions, the quantum yield of the initial breaking of a Ru–N(bpy) bond changed 7 fold depending on the kind of X
− in the order, CF
3SO
3− < NO
3− < HSO
4− < Cl
− < Br
−. In HCl–NaCl system it increased linearly with increasing [Cl
−]. The photosubstitution must have proceeded with a mechanism of associative nature.
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Toshishige M. Suzuki, Chiyoko Chida, Masatoshi Kanesato, Toshiro Yokoy ...
1989 Volume 18 Issue 7 Pages
1155-1158
Published: 1989
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A new composite material based on hydrous zirconium oxide and a porous polymer resin has been prepared by the impregnation of tetra(n-butoxy)zirconium into porous polymer beads followed by hydrolysis of the alkoxide. The adsorption properties of the Zr-loaded resin for fluoride ion have been described.
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Masashi Oshima, Hatsumi Mori, Gunzi Saito, Kokichi Oshima
1989 Volume 18 Issue 7 Pages
1159-1162
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The electrochemical oxidation of BEDT-TTF with Hg(SCN)
2, KSCN, and 18-crown-6 ether yielded two different BEDT-TTF salts of mercury(II) thiocyanate depending on the solvent used. The K
+ containing salt, (BEDT-TTF)
2[KHg(SCN)
4], was metallic down to 1.5 K with various temperature dependences. The crystal structures showed an alternating stacking of two-dimensional networks of BEDT-TTF molecules and of KHg(SCN)
4 anions. The other modification (BEDT-TTF)
3[Hg(SCN)
3] exhibited metal-insulator (MI) transition at around 180 K.
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Shin-ichi Sasaoka, Takashi Joh, Tadasu Tahara, Shigetoshi Takahashi
1989 Volume 18 Issue 7 Pages
1163-1166
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Dicarbonyl(η
3-1,1,2,3,4,4-hexafluoro-2-butenyl)(triphenyl-phosphine)cobalt(I) was isolated at the first time from the reaction of tetracarbonylhydridocobalt(I) with hexafluorobuta-1,3-diene and triphenylphosphine.
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Akira Tatehata, Tsuyoshi Mitani
1989 Volume 18 Issue 7 Pages
1167-1170
Published: 1989
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The stereoselectivities in the electron-transfer reactions of [Co(en)
3]
2+ with eight Δ anionic Co(III) complexes in aqueous solution have been determined by observing the enantiomeric excesses of the [Co(en)
3]
3+ product. The results are compared with the ion-pairing stereoselectivity between [Co(en)
3]
3+ and the anionic complexes. Even the Δ anionic complexes which form favorable pairs with Δ-[Co(en)
3]
3+ yielded the excesses of Λ-[Co(en)
3]
3+ product.
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Teruaki Mukaiyama, Ryuichiro Hara
1989 Volume 18 Issue 7 Pages
1171-1174
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In the presence of a catalytic amount of [1,2-benzenediolato(2−)-
O,
O′]oxotitanium, ketene silyl acetals smoothly react with α,β-unsaturated ketones to afford the corresponding Michael adducts in high yields.
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Michiya Ota, Sugio Otani, Kiyoshi Kobayashi
1989 Volume 18 Issue 7 Pages
1175-1178
Published: 1989
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Thermosetting resins composed of triarylmethane structure were prepared by heating a mixture of a polycyclic aromatic compound and an aromatic aldehyde in the presence of an acid catalyst. The resin prepared from the mixture of pyrene and terephthalaldehyde exhibited scarcely any weight loss up to 530 °C under nitrogen. While the resin from anthracene has such high carbon yield as 70% at 800 °C, although its thermostability is somewhat inferior.
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Michiya Ota, Sugio Otani
1989 Volume 18 Issue 7 Pages
1179-1182
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A thermosetting resin composed of triarylmethane structure was prepared under a magnetic field. The resulting resin exhibited ferromagnetic properties with excellent reproducibility.
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Michiya Ota, Sugio Otani, Michiya Igarashi
1989 Volume 18 Issue 7 Pages
1183-1186
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Organic ferromagnets have been successfully prepared by dehydrogenation from the triarylmethane resins and the irradiation with ultraviolet or laser light in the presence of photo-oxidizing agent is found to be effective to the dehydrogenation.
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Koichi Narasaka, Fumihiko Kanai, Makoto Okudo, Norikazu Miyoshi
1989 Volume 18 Issue 7 Pages
1187-1190
Published: 1989
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Kinetic resolution of racemic α-arylcarboxylic acids is successfully achieved by a catalytic use of titanium tetraisopropoxide and a chiral 1,4-diol in the reaction of the corresponding 2-pyridinethiol esters and isopropyl alcohol.
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Takashi Ishihara, Koichi Yamaguchi, Manabu Kuroboshi
1989 Volume 18 Issue 7 Pages
1191-1194
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1-Substituted
F-1-alkenyl phosphates, prepared easily from
F-alkyl ketones, were treated with diisobutylaluminium hydride in tetrahydrofuran at 0 °C for 5 min or at room temperature for 30 min to generate quantitatively the corresponding ketone aluminium(III) enolates, which underwent the aldol reaction with various aldehydes at 0 °C to give α-fluoro-α-
F-alkyl β-hydroxy ketones in good to excellent yields.
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Masaaki Iwata, Hiroyoshi Kuzuhara
1989 Volume 18 Issue 7 Pages
1195-1198
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Secondary formamides were found to be favorable sources for the efficient oxygenation site via
N-nitrosation. Thermal reaction (85 °C in benzene) of
N-nitroso formamides proceeded effectively to provide the corresponding formates in good yields, which, then, were hydrolyzed to alcohols under weakly basic conditions. In treatment of optically active formamide, the corresponding alcohol was isolated with 72% retention of configuration.
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Yukito Murakami, Jun-ichi Kikuchi, Teruhisa Ohno, Takayuki Hirayama, H ...
1989 Volume 18 Issue 7 Pages
1199-1202
Published: 1989
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A cubic cyclophane surrounded by six faces, each being constructed with the [3.3.3.3]azaparacyclophane ring, behaved as a polycationic host in acidic aqueous media and exhibited pH-dependent binding behavior toward an anionic guest, ANS, since microenvironmental properties of the host cavity are varied by the extent of protonation at the nitrogen atoms.
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Kazuhiko Saigo, Kazuaki Kudo, Yukihiko Hashimoto, Nobuhiro Kihara, Mas ...
1989 Volume 18 Issue 7 Pages
1203-1206
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α,β,γ,δ-Unsaturated esters were conveniently synthesized from ethyl sulfolane-2-carboxylate through alkylation and oxidation followed by the retro Diels–Alder reaction of the resulting 3-sulfolene derivatives. The reaction proceeded with high
E,
E-selectivity.
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Taku Nakano, Yoshitaka Kitamura
1989 Volume 18 Issue 7 Pages
1207-1210
Published: 1989
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A new autoreduction system of hemin was established in the case of synthetic hemins with hydroquinone and isocyanide. The reduction of hemin needed both of hydroquinone and isocyanide. Kinetic studies suggested that a six-coordinated and low-spin iron porphyrin complex was an intermediate of the reduction.
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Masashi Kijima, Masahiro Kato, Takeo Sato
1989 Volume 18 Issue 7 Pages
1211-1214
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A new method for investigating the redox behavior of powdery polymer carrying cobaloxime is described. Benzylcobaloxime and chlorocobaloxime are each immobilized into cross-linked poly(4-vinylpyridine). Insoluble polymers soaked in an electrolyte solution are set on a platinum working electrode. The redox behaviors of these cobaloximes were recorded in a solid state by cyclic voltammetry.
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Gorou Arai, Tomitaka Harashina, Iwao Yasumori
1989 Volume 18 Issue 7 Pages
1215-1218
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CO
2 was electrochemically reduced to CH
3OH in aqueous Na
2SO
4 solution on a Ru-modified glassy carbon electrode. Ru was fixed on poly(hydroquinone/
p-benzoquinone) prepared by electropolymerization of mercaptohydroquinone. The reduction of CO
2 proceeded with markedly low overvoltage, starting at −0.5 V vs. SCE at room temperature. The current efficiency for CH
3OH formation attained ca. 100% at −0.7 V vs. SCE with a current density of ca. 0.2 mA/cm
2.
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Akira Tanaka, Masashi Yamaguchi, Takashi Iwasaki, Keiji Iriyama
1989 Volume 18 Issue 7 Pages
1219-1222
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A new replica method for transmission electron microscopy with plasma polymerized film by glow discharge was originally developed. The method was found to be applicable for the surface observation of Langmuir–Blodgett film.
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Tadafumi Uchimaru, Seiji Tsuzuki, Kazutoshi Tanabe, Kensuke Furukawa, ...
1989 Volume 18 Issue 7 Pages
1223-1226
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Ab initio and semi-empirical calculations were carried out on keto/enol tautomers of 6-methyl-7,8-dihydropterin, a model compound for the natural substrate of dihydrofolate reductase. The most likely conformer of pterin ring (inner enol
3) during the hydride transfer from NADPH was computationally chracterized.
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Shunichi Fukuzumi, Masashi Ishikawa, Toshio Tanaka
1989 Volume 18 Issue 7 Pages
1227-1230
Published: 1989
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The pH dependences of the second-order rate constants and the primary kinetic isotope effects for hydride-transfer reactions from an acid-stable NADH model compound, 10-methylacridan (AcrH
2), to a series of
p-benzoquinone derivatives (Q) in H
2O–EtOH (5:1 v/v) have revealed that the hydride transfer proceeds
via acid-catalyzed electron-transfer from AcrH
2 to Q.
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Shunichi Fukuzumi, Toshiaki Kitano, Toshio Tanaka
1989 Volume 18 Issue 7 Pages
1231-1234
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10-Methylacridinium ion (AcrH
+) is reduced efficiently by fatty acids (RCOOH) in the presence of a base in acetonitrile to yield 9-alkyl-10-methylacridan selectively under irradiation with visible light
via photoinduced electron transfer from RCOO
− to the singlet excited state of AcrH
+.
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Shuji Tomoda, Yoshinosuke Usuki
1989 Volume 18 Issue 7 Pages
1235-1236
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Treatment of alkenes with the reagent generated by the reaction of silver(I) fluoride with benzeneselenenyl bromide under ultrasound irradiation afforded 2-fluoroalkyl selenides in decent yields.
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Noboru Ono, Kazuhiro Maruyama
1989 Volume 18 Issue 7 Pages
1237-1240
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Acid catalyzed cyclization of 2-(hydroxymethyl)pyrroles with electron-donating substituents at the β-position gives a mixture of four isomers of porphyrins (type I-IV) in the homogeneous reaction. The isomerization during cyclization can be minimized in the heterogeneous reaction using silica gel as an acid catalyst to give type I porphyrins selectively.
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Yashwant D. Vankar, Rajendra K. Saksena, Anita Bawa
1989 Volume 18 Issue 7 Pages
1241-1244
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1,2-Diones and α-iodoketones have been prepared from α-nitroepoxides by treatment with DMSO/BF
3·Et
2O followed by Et
3N and BF
3·Et
2O/NaI respectively.
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Takeshi Yamamura, Makoto Tadokoro, Reiko Kuroda
1989 Volume 18 Issue 7 Pages
1245-1246
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A simple route to the nickel complex of thiosalen, Ni(tsalen), which is the correspondent of the classical
salen compound, was developed. The molecular structure of Ni(tsalen) was studied also.
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Masahiro Fujiwara, Akio Baba, Haruo Matsuda
1989 Volume 18 Issue 7 Pages
1247-1250
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Azilidine–trimethylsilyl bromide–tetraphenylstibonium bromide system is an effective reagent to produce silyl enol ethers from cyclic ketones. This had the specific selectivity to silylate cyclic ketones exclusively even in the case of coexsisting with acyclic ketones.
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Naohide Matsumoto, Keiji Inoue, Hisashi Okawa, Sigeo Kida
1989 Volume 18 Issue 7 Pages
1251-1254
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Imidazolate-bridged copper(II)–chromium(III)–copper(II) complex, [Cu(A)Cr(salen)Cu(A)]ClO
4·3H
2O, has been synthesized and characterized, where H
2A = 4-(6-methyl-8-oxo-2,5-diazanona-1,5,7-trienyl)imidazole and H
2salen =
N,
N′-di(salicylidene)ethylenediamine, respectively. The magnetic moment per molecule increases from 4.61 BM at 297.8 K to the maximum value 5.27 BM at 14 K, and then decreases to 4.42 BM at 4.4 K. The magnetic behavior shows that there operates a ferromagnetic interaction between chromium(III) and copper(II) ions through imidazolate group.
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Tamotsu Fujisawa, Akihiko Tanaka, Yutaka Ukaji
1989 Volume 18 Issue 7 Pages
1255-1256
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The conjugate addition of halide anion to acetylenic ketones proceeded by the combined use of cerium salts, halotrimethylsilanes and sodium or tetrabutylammonium salts to afford
trans-β-halo enones stereoselectively. On the other hand,
N,
N-diethyl
cis-β-haloacrylamides were synthesized from propiolamide.
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Takeshi Takeda, Sinji Ogawa, Masatoshi Koyama, Tetsuya Kato, Tooru Fuj ...
1989 Volume 18 Issue 7 Pages
1257-1260
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γ,δ-Unsaturated ketones were obtained by the reaction of trimetylsilyl enol ethers with allylstannanes in the presence of tin(IV) or copper(II) salt in good yields.
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Yoshihiko Ito, Masahiko Inouye, Masahiro Murakami
1989 Volume 18 Issue 7 Pages
1261-1264
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A stepwise introduction of two different alkynyl groups onto the iminocarbon leading to the synthesis of unsymmetrical dialkynyl imines was achieved by palladium-catalyzed coupling reaction of
N-phenyl phenylthioimidoyl chloride with alkynyltin compounds.
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Kiyonori Shinoda, Kensei Yasuda, Minoru Ohta
1989 Volume 18 Issue 7 Pages
1265-1266
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Polychlorobiphenyl (PCB) was transchlorinated with benzene into biphenyl and chlorobenzene in the presence of palladium(II) chloride/cerium(III) chloride supported on activated charcoal. The transchlorination proceeded smoothly for a long time at 375 °C.
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Takuzo Funabiki, Motoyoshi Tsujimoto, Satoshi Ozawa, Satohiro Yoshida
1989 Volume 18 Issue 7 Pages
1267-1268
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Hydroquinones have been found to be useful as reductants for one-step hydroxylation of aromatic compounds by nonheme iron complex with activation of O
2 in anhydrous organic solvents. The iron complex is easily prepared by mixing FeCl
3, pyrocatechol, and pyridine. The efficiency of hydroquinones as reductants is greatly dependent on the substituent:
t-Bu- > 2,5-
t-Bu
2- >>
H-hydroquinone.
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