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Tetsuya Kajimoto, Masami Yamashita, Yohko Imamura, Kokichi Takahashi, ...
1989 Volume 18 Issue 4 Pages
527-530
Published: 1989
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Novel phenolics HM-1(
3), HM-2(
5), HM-3(
6), and HM-4(
7) were obtained from phytopathogenic fungus
Helicobasidium mompa which causes violet root rot against mulberry and several kinds of fruit trees. Compounds
3 and
7 could be precursors of helicobasidin and deoxyhelicobasidin, which have already been isolated from the same oriqin, while
5 and
6 were unusual types of
C15-compound.
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Young-Chul Kim, Wataru Ueda, Yoshihiko Moro-oka
1989 Volume 18 Issue 4 Pages
531-534
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Various mixed metal oxide catalysts were tested for the oxidation of propane to acrolein. An Ag-doped bismuth vanadomolybdate catalyst was found to be most effective among the catalysts tested; the selectivity to acrolein reached to more than 60% at 13% conversion of propane.
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Yasushi Murakami, Kiyoshi Otsuka, Yuji Wada, Akira Morikawa
1989 Volume 18 Issue 4 Pages
535-538
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B
2O
3–Al
2O
3, B
2O
3–MgO, B
2O
3–La
2O
3, and B
2O
3–P
2O
5 are selective catalysts for the partial oxidation of ethane. Among these catalysts, B
2O
3(30wt%)-added Al
2O
3 showed the highest catalytic activity in the formations of acetaldehyde (yield 1.03%) and ethylene (14.6%). Acetaldehyde is formed not via ethylene but directly from ethane. The formations of ethylene and acetaldehyde occur on different active sites.
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Shuji Tanabe, Hiroshige Matsumoto
1989 Volume 18 Issue 4 Pages
539-542
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The formation and catalytic behavior of active species in CuY zeolite were investigated with aids of TPR and EXAFS measurements. The active species formed during a reduction–reoxidation treatment was directly and reversibly reduced to Cu metal clusters with CO, indicating that the CO oxidation on the zeolite proceeded via the redox mechanism of active CuO clusters.
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Akio Tada, Yutaka Watarai, Katuhiro Takahashi, Yuzo Imizu, Hidenobu It ...
1989 Volume 18 Issue 4 Pages
543-546
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The activities and selectivities of Ni–Cu/SiO
2 catalysts for the titled reaction were investigated. The binary metal catalysts exhibited much higher performances than Ni/SiO
2 and Cu/SiO
2. In particular, 100% conversion and 100% CO selectivity were obtained over Ni
0.1Cu
0.9/SiO
2 at a reaction temperature as low as 280 °C during the process time of 96 h.
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Hideki Obi, Tadashi Segawa, Takao Yotsuyanagi
1989 Volume 18 Issue 4 Pages
547-550
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Gallium(III) was extracted as Q
3[GaL
3] from 1–4 mol/dm
3 NaOH solutions by the combined use of
o-dihydroxy derivatives of benzene or naphthalene (H
2L) and asymmetric quarternary ammonium ions (Q
+) having at least one methyl-group. Hydrophobic large alkyl groups are an essential constituent of the extractant, while disposition of them is not necessarily restricted on the ligands (H
2L), but on the counter ions (Q
+). These findings provide a new basis for designing the reagent suitable for the ion-association extraction of metal ion from the strongly alkaline media.
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Masahide Yasuda, Yoriaki Matsuzaki, Toshiaki Yamashita, Kensuke Shima
1989 Volume 18 Issue 4 Pages
551-554
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Salt Effects on arene/
p-dicyanobenzene exciplexes which undergo photoamination of arenes with aliphatic amines in the presence of tetra-
n-butylammonium tetrafluoroborate are investigated. From a kinetic analysis it is found that the photoamination proceeds via charge-separation of the exciplexes with the salt followed by nucleophilic addition of aliphatic amines.
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Masayuki Kuzuya, Atsuo Koide, Akiko Ito, Akihiro Noguchi
1989 Volume 18 Issue 4 Pages
555-558
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The room temperature ESR spectra of the radicals in four kinds of plasma-irradiated acrylic resins, PMMA, PMAA, and their copolymers, were studied. The spectra of the copolymers have shown unique patterns and the spectral intensity was proportional to the relative amount of carboxylic acid group in acrylic resins.
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Hisashi Takahashi, Naoko Yamamoto, Hideo Takeda, Kazuo Achiwa
1989 Volume 18 Issue 4 Pages
559-562
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The effects of
cis-coordinating phosphine of the rhodium complexes of BCPM ((2
S,4
S)-
N-(
t-butoxycarbonyl)-4-(dicyclohexylphosphino)-2-[(diphenylphosphino)methyl]pyrrolidine) analogues bearing electron donating or attracting groups on the catalytic activities in the asymmetric hydrogenation of itaconic acid are described.
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Masahiko Saburi, Youichi Ishii, Nobutarp Kaji, Tsuneo Aoi, Ichiro Sasa ...
1989 Volume 18 Issue 4 Pages
563-566
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Highly selective hydrogen transfer reaction of substituted diols catalyzed by RuH
2(PPh
3)
4 was applied to the conversion of aldopentoses into their stereoisomers via protected pentitols. Thus, the selective transformations of
L-arabinose and
L-ribose into protected
L-lyxonolactone and
D-ribonolactone, respectively, were achieved.
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Taichi Nakano, Yurika Ino, Yoichiro Nagai
1989 Volume 18 Issue 4 Pages
567-568
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A series of new γ-alkyl-α-hydroxy-γ-lactones which are promising as excellent food intake-control substances was synthesized in high yields by the hydrolysis of γ-alkyl-α-chloro-γ-lactones.
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Shigeru Isayama, Teruaki Mukaiyama
1989 Volume 18 Issue 4 Pages
569-572
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In the presence of a catalytic amount of bis(trifluoroacetylacetonato)cobalt(II), various olefins react smoothly with molecular oxygen (oxidant) and triethylsilane (reductant) to afford the corresponding alcohols regioselectively in good yields along with ketones.
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Shigeru Isayama, Teruaki Mukaiyama
1989 Volume 18 Issue 4 Pages
573-576
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In the presence of a catalytic amount of bis(1,3-diketonato)cobalt(II), various olefins react with molecular oxygen and triethylsilane at room temperature to give the corresponding triethylsilyl peroxides in high yields under neutral conditions. The reaction provides a new method for the preparation of various peroxides directly from olefins.
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Isao Shimizu, Hirotoshi Ishii
1989 Volume 18 Issue 4 Pages
577-580
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α-Fluoroketones, α-fluoro-α-allylketones, and α-fluoro-α,β-unsaturated ketones are synthesized by palladium-catalyzed decarboxylation reactions of allyl α-fluoro-β-keto carboxylates.
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Koji Araki, Seiji Shinkai, Tsutomu Matsuda
1989 Volume 18 Issue 4 Pages
581-584
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Activation parameters for calixarene ring inversion were determined for the first time by computer-assisted simulation of the
1H-NMR spectra. It was found that the process is governed by the enthalpy term and features small, negative ΔS
≠ for calix[4]arenes and positive ΔS
≠ for calix[8]arenes. These data are of great significance to understanding the nature of calixarene conformations.
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Hiromi Matsuhashi, Kenji Sakurai, Kazushi Arata
1989 Volume 18 Issue 4 Pages
585-586
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Sodium doped ZrO
2 was studied as the methane activation catalyst and found to be highly active at low temperature giving C
3 hydrocarbons as main products. Among the catalysts tested, 4.3 mol% Na
+ doped ZrO
2 showed the best conversion (18.2%) and selectivity (59.0%) for the formation of C
2 and C
3 hydrocarbons at 873 K; the yield of C
3 was 7.5% with ratio 3.3 of propane/propene.
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Koushi Fukunishi, Satoshi Kitamura, Masaki Kuwabara, Hiroki Yamanaka, ...
1989 Volume 18 Issue 4 Pages
587-590
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The rates and the activation parameters for the thermal
cis-to-
trans isomerization of 5,5′-dialkylthioindigo dyes embedded in a smectic mesophase of butyl stearate were affected by the transition of the liquid-crystalline to the isotropic phase, depending upon the alkyl length.
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Akira Mori, Minoru Uchida, Hitoshi Takeshita
1989 Volume 18 Issue 4 Pages
591-592
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Compounds having liquid crystal properties with a tropolone core were synthesized: A series of 5-alkoxy-2-benzoyloxytropones showed the mesophase(s), whereas corresponding 5-alkoxy-2-benzyloxytropones did not. A [1,9] sigmatropy seems to play an important role to this mesomorphic behavior.
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Tamiko Takahashi, Toru Hagi, Kazuyoshi Kitano, Yoshio Takeuchi, Toru K ...
1989 Volume 18 Issue 4 Pages
593-596
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2α- and 2β-Tropanols were synthesized by 1,3-dipolar cycloaddition of phenyl vinyl sulfone and 1-methyl-3-oxidopyridinium regio- and stereoselectively. The method was extended to a preparation of 6α-fiuoro-2β-tropanol from 1-(benzenesulfonyl)-1-fluoroethene.
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Tamiko Takahashi, Kazuyoshi Kitano, Toru Hagi, Hiroko Nihonmatsu, Toru ...
1989 Volume 18 Issue 4 Pages
597-598
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The first enantioselective synthesis of (1
S)-(−)-2α-tropanol, which has the opposite absolute configuration to that of natural cocaine, was achieved by an asymmetric 1,3-dipolar cycloaddition of (
R)
s-
p-tolyl vinyl sulfoxide and 1-methyl-3-oxidopyridinium.
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Sannamu Lee, Nam Gyu Park, Tamaki Kato, Haruhiko Aoyagi, Tetsuo Kato
1989 Volume 18 Issue 4 Pages
599-602
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A helix-breaker amino acid, proline, was introduced into an antimicrobial peptide, Ac–(L–Leu–L–Ala–L–Arg–L–Leu)
3–NHCH
3 (4
3). The peptides [Pro
6]4
3 (1), [Pro
2,6]4
3 (2), and [Pro
2,6,10]4
3 (3) were able to form α-helix in order of 1 > 2 > 3 in the presence of acidic liposomes, indicating that proline does not always behave as a strong helix-breaker in specific surroundings. The antimicrobial activity was found to be connected closely with their amphipathic property.
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Hiroyuki Ishibashi, Hiroshi Sakashita, Satoko Morita, Sumiyo Mitani, M ...
1989 Volume 18 Issue 4 Pages
603-606
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Treatment of trimethylphenylsilane with methyl chloro(methylthio)acetate in the presence of atannic chloride gave a mixture of the alkylated silylbenzenes, in which the
meta- and
para-substituted products predominated. The partial rate factors of this reaction suggest that the trimethylsilyl group slightly activates the
meta- and
para-positions of the silylbenzene.
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Kazuaki Sasaki, Yoshio Aso, Tetsuo Otsubo, Fumio Ogura
1989 Volume 18 Issue 4 Pages
607-610
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Diisobutylaluminium benzenetellurolate, prepared from diphenyl ditelluride and diisobutylaluminium hydride, easily added to α,β-unsaturated carbonyl compounds in 1,4-fashion to give β-phenyltelluro carbonyl compounds. The intermediate aluminium enolates reacted with aldehydes to give aldol adducts. Subsequent telluroxide elimination resulted in the formation of α-substituted α,β-unsaturated carbonyl compounds.
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Yumiko Kaku, Masami Otsuka, Masaji Ohno
1989 Volume 18 Issue 4 Pages
611-614
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cis-β-Methylstyrene is oxidized either with the Fe(III)–H
2O
2 or with the Fe(II)–O
2 complex systems of bleomycin and the synthetic model ligand PYML-6 to give optically active epoxide, showing that the environment around the iron-nucleus is chiral enough to cause asymmetric epoxidation.
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Keiji Itoh, Saburo Nakanishi, Yoshio Otsuji
1989 Volume 18 Issue 4 Pages
615-618
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1,4-Acylation-alkylation of 1,3-dienes occurred regioselectively via (η
3-1-acetonylallylic)Fe(CO)
2NO complexes upon treatment of 1,3-dienes with iodomethane in the presence of Bu
4NFe(CO)
3NO and then with carbon nucleophiles or carbon electrophile.
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Ikuya Shibata, Tomoyuki Yoshida, Akio Baba, Haruo Matsuda
1989 Volume 18 Issue 4 Pages
619-622
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Bu
3SnH–HMPA combined system is an efficient reagent for the reduction of aldehydes. The reaction proceeds in good yields, and chemoselective carbonyl reduction is achieved for the substrate which includes another reducible group. Moreover, the intermediate, tin alkoxide, undergoes further reaction such as the preparation of ethers and heterocyclic compounds in the one pot procedure.
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Tsutomu Morikawa, Masayuki Uejima, Yoshiro Kobayashi
1989 Volume 18 Issue 4 Pages
623-624
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A trifluoromethyl-substituted carbon radical, generated by radical deoxygenation of α-trifluoromethyl alcohol, intramolecularly formed C–C bond to give a five- or six-membered cyclic compound.
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Hiromichi Ohta, Shinsuke Matsumoto, Yasushi Okamoto, Takeshi Sugai
1989 Volume 18 Issue 4 Pages
625-628
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2-Alkoxyethyl phenyl sulfides were oxidized by incubation with
Rhodococcus equi IFO 3730 to afford chiral sulfoxides of high enantio excess. Phenyl vinyl sulfoxide and 2-hydroxyethyl phenyl sulfoxide were obtained from microbial oxidation products without any loss of their optical purities.
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Jung Ho Park, Sunggak Kim
1989 Volume 18 Issue 4 Pages
629-632
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Magnesium bromide in ether is found to be a very effective and highly selective reagent for the conversion of acetals into the corresponding thioacetals in the presence of ketones.
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Sadayuki Himeno, Toshitaka Hori, Atsuyoshi Saito
1989 Volume 18 Issue 4 Pages
633-636
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The title compound was isolated from a 0.15 M (= mol/dm
3) Mo(VI)/0.3 M H
3PO
3/0.1 M HCl/60% (v/v) CH
3COCH
3 system. The existence of a new type of heteropoly complex with a composition of Mo/P = 6/5 was elucidated. The formation conditions and the IR spectroscopic characteristics were compared with those of well-established pentamolybdodiphosphonate.
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Etsuo Kokufuta, Katsuhiro Sumi, Wen-Chin Wu
1989 Volume 18 Issue 4 Pages
637-640
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Ferric complex of tetraphenylporphyrin is useful as a carrier for preparing a bulk liquid membrane system in which SCN
− ion is selectively transported against its concentration gradient by coupling with the flow of OH
− ion coming from the opposite direction.
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Masaki Hasegawa, Akira Kunita, Chanmoon Chung, Keiichi Hayashi, Sadao ...
1989 Volume 18 Issue 4 Pages
641-644
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Methyl and ethyl α-cyano-4-[2-(2-pyridyl)ethenyl]cinnamate crystals were highly photoreactive and formed the cycloadduct having an alternating zigzag and linear chain structures accompanied with topochemical induction of the two chiralities alternatively in the chain from the β-type achiral crystal of prochiral molecules.
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Masakatsu Nomura, Toru Ida, Mikio Miyake, Takashi Kikukawa, Tatsuhisa ...
1989 Volume 18 Issue 4 Pages
645-648
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Curie-point pyrolysis-GC analyses were applied for structural analyses of hexane-soluble (HS) and hexane-insoluble and benzene-soluble (HI-BS) fractions from two SRC samples. Pyrograms of HS and HI-BS fractions are strikingly similar, indicating that they are composed of similar aromatic constituents, although the molecular weight distributions between the two fractions are different. The difference in coal rank for the two SRC samples was reflected as the profiles of pyrograms.
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Hiromitsu Terao, Tsutomu Okuda
1989 Volume 18 Issue 4 Pages
649-652
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The single-crystal Zeeman effect was investigated for the
81Br NQR lines in the mixed-valence compound (NH
4)
4Sb
IIISb
vBr
12 at room temperature. Comparing with the results of X-ray analysis, it was concluded that the Sb
IIIBr
63− ions possess D
2d symmetry and the Sb
vBr
6− ions possess D
4h (nearly O
h) symmetry.
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Tsutomu Inoue, Seiichi Inoue, Kikumasa Sato
1989 Volume 18 Issue 4 Pages
653-656
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o-(1-(Alkylthio)alkyl)phenols are converted into
o-quinone methides in good yield by treatment with silver oxide under mild conditions. Since the methides tend to prefer (
E) configuration,
cis-4-alkyl-2-alkoxychromans are exclusively obtained as a result of
endo [4+2] cycloaddition of the methides and vinyl ethers.
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Mamoru Ai
1989 Volume 18 Issue 4 Pages
657-658
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Various kinds of Mo-based oxides were tested as catalysts for the vapor-phase oxidation of α-methylstyrene to form phenylacrolein (atropoaldehyde). The best performance was obtained with the Te/Mo atomic ratio = 0.4 catalyst; the one-pass yield of phenylacrolein attained 48.5 mol% at the α-methylstyrene conversion of 96.3%.
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Yukio Masaki, Ikuhiro Iwata, Isao Mukai, Hirohisa Oda, Hiromu Nagashim ...
1989 Volume 18 Issue 4 Pages
659-662
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Protection of various types of alcohols with
p-anisyloxymethyl (
p-AOM) chloride gave the corresponding
p-AOM ethers which were deprotected with ceric ammonium nitrate efficiently. Chemoselective removal either of
p-AOM group or of tetrahydropyranyl group is also reported.
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Masaru Ishida, Takamichi Aoyama, Shinzi Kato
1989 Volume 18 Issue 4 Pages
663-666
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5-Phenylthio-1,3-cyclopentadiene reacted with maleic anhydride to give a 4 : 6 mixture of
syn- and
anti-attack adducts. In contrast, the selenium isologue, 5-phenylseleno-1,3-cyclopentadiene reacted with dienophiles with remarkable
anti-π-facial selectivity to give the corresponding
anti-attack adducts, exclusively.
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Jun-ichiro Setsune, Mitsuhiro Ikeda, Yoshihiro Ishimaru, Teijiro Kitao
1989 Volume 18 Issue 4 Pages
667-670
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Acetylene is reversibly inserted into a Co–N bond of bis(aquo)octaethylporphyrinatocobalt(III) perchlorate, (OEP)Co
III(H
2O)
2ClO
4 (
1), in CH
2Cl
2 solution, generating a d
6 high spin (S = 2) complex. Addition of 2,6-lutidine to a mixture of
1 and acetylene gave a σ-vinylcobalt(III) complex, (OEP)Co
III–CH=CH–L
+ClO
4 [L = 2,6-lutidine], whereas pyridine replaced the acetylene ligand to afford (OEP)Co
III(PY)
2ClO
4. These results suggest the intermediacy of a Co
III acetylene π-complex.
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Jun-ichiro Setsune, Yoshihiro Ishimaru, Yasushi Saito, Teijiro Kitao
1989 Volume 18 Issue 4 Pages
671-674
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Bis(aquo)tetra(
p-tolyl)porphinatocobalt(III) perchlorate reacted immediately with acetylene, in the absence and presence of tetra(
p-tolyl)porphinatocobalt (II), to give a N,N′-vinylene linked bisporphyrin biscobalt(II) complex and a Co,N′-vinylene linked bisporphyrin cobalt(III) complex (
4b), respectively. (
4b) was oxidatively converted into N,N′-vinylene linked bisporphyrin free base. An octaethylporphyrin analogue corresponding to
4b was obtained when a mixture of bis(aquo)octaethylporphyrinatocobalt(III) perchlorate and octaethylporphyrin was allowed to react with acetylene gas.
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Eiji Wada, Shuji Kanemasa, Otohiko Tsuge
1989 Volume 18 Issue 4 Pages
675-678
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Remarkable rate enhancement is achieved by use of a weak Lewis acid catalyst such as zinc chloride or bromide in the hetero Diels–Alder reactions of 2-oxo-3-alkenylphosphonates as readily enolizable 1-oxa-1,3-dienes with vinyl ethers. Highly endo-selective cyclo-adducts, 2,4-
cis-3,4-dihydro-2
H-pyrans, are produced in good yields.
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Tetsuya Kajimoto, Kazumi Yokomizo, Kiyoshi Yahiro, Toshiko Umeda, Shoz ...
1989 Volume 18 Issue 4 Pages
679-680
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Halo-toxin was isolated from the incubated medium of
pseudomonas syringae pv.
mori which causes halo bright disease against the leaves of mulberry trees. The structure of this compound was revealed to be Pro-Phe-Pro-Gly-Pro-Ile by spectroscopic means and amino acid sequence analysis.
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Kaoru Fujimoto, Ikusei Nakamura, Kohshiroh Yokota
1989 Volume 18 Issue 4 Pages
681-682
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It was pointed out that Ga promote the zeolite-promoted aromatization of lower paraffin by “Reverse Spillover Effect” of hydrogen. A new hybrid catalyst which was comparable to Ga-ZSM-5 for the title reaction was developed on this concept.
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Masahiro Tada, Masashi Nagai, Chieko Okumura, Yasuko Osano, Takao Mats ...
1989 Volume 18 Issue 4 Pages
683-686
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A novel metabolite spiro-compound, hyperolactone was isolated from stems and leaves of
Hypericum chinense L. The structure was deduced by 2D-NMR experiment, chemical transformation and finaly by X-ray crystallography.
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Hiroaki Yanagisawa, Takuro Kanazaki, Takahide Nishi
1989 Volume 18 Issue 4 Pages
687-690
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Statine, (3
S,4
S)-4-amino-3-hydroxy-6-methylheptanoic acid, and its analogues were prepared from 5,6-anhydro-3-deoxy-1,2-
O-isopropylidene-
D-glucofuranose. The key step is the stereospecific reaction of the epoxy sugar with the Grignard reagent.
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Masakazu Yamashita, Haruyoshi Tashika, Rikisaku Suemitsu
1989 Volume 18 Issue 4 Pages
691-692
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Alkyl vinyl ketones were hydroacylated by organotetracarbonylferrates to the corresponding 1,4-diketones in good yields in dipolar aprotic solvents such as dimethylacetamide. The addition of 18-Crown-6 made an increase of the yields.
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Tatsuo Ohgushi, Manabu Miyoshi
1989 Volume 18 Issue 4 Pages
693-696
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Properties of (Na,Ca)-A zeolites treated in a deep-bed and shallow-bed were compared with each other. Adsorptive capacities for water linearly increased with increasing of a Ca content in the deep-bed zeolites but not in the shallow-bed zeolites. Thermal stabilities of the zeolites were lowered by the deep-bed treatment but not by the shallow-bed one. Differences in the properties of both zeolites were related to rearrangement of Ca
2+ ions.
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Kenichi Yamamoto, Yoichi Iitaka
1989 Volume 18 Issue 4 Pages
697-698
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The structure of synthetic nitro-5,10,15,20-tetraphenylporphyrinato(piperidine)cobalt(III) has been determined by X-ray diffraction method. The results revealed that the porphyrin plane is markedly distorted to nonplanar due to the steric interaction between the axial piperidine and the porphyrin core.
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Hiroyuki Itoh, Toshiya Saito, Manabu Shizuta, Eiichi Kikuchi
1989 Volume 18 Issue 4 Pages
699-702
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Liquid phase methanol synthesis was carried out over ultrafine particle (UFP) catalysts. A very high activity was obtained over Zn UFP modified using Cu acetylacetonate and LiAlH
4. The rate of methanol formation on this catalyst at the steady state was about 1.8 times as high as that of a co-precipitated catalyst.
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