Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
Volume 66 , Issue 6
Showing 1-50 articles out of 56 articles from the selected issue
  • Mahendra Lal Srivastava, Bali Ram
    Type: Accounts
    Subject area: AI
    1993 Volume 66 Issue 6 Pages 1593-1597
    Published: 1993
    Released: August 07, 2006
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    Studies on hydrodynamic and electroosmotic permeation of water, aqueous solutions of D-glucose and urea in the concentration range 10−4 to 10−3 mol dm−3 across progesterone plug membrane have been carried out to characterize the electrical nature of interface. Phenomenological coefficients have been evaluated from the linear and nonlinear equations obtained. Membrane properties viz., pore radius and zeta potentials have been determined using these coefficients. The nonlinear variation of electroosmotic flow in case of aqueous solutions of urea has been explained on the basis of electrical double layer theory and the structural modifications that are likely to occur at membrane–solution interface because of solute–solvent, solvent–solvent, and membrane–permeant interactions.
  • Masafumi Yoshida, Noriyuki Sakamoto, Kimiyoshi Ikemi, Shizuo Arichi
    1993 Volume 66 Issue 6 Pages 1598-1602
    Published: 1993
    Released: August 07, 2006
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    Measurements of the light scattering and viscosity of poly(2-vinylpyridine) (P2VP) in an aqueous (aq) solution of H2SO4 at 25 °C were carried out. Although from Stockmayer–Fixman’s theory the characteristic ratio (C) was found to be almost constant over the range from 0.1 M to 5.1 M H2SO4, the long-range interaction parameter was found to change through the minimum. The difference among the interaction parameters of P2VP and those of poly(4-vinylpyridine) (P4VP) reported before is discussed. Both the second virial coefficient (A2) and the mean-square radius of gyration (<s2>) of the atactic P2VP sample based on a light-scattering measurement decreased at first with increasing concentration of H2SO4, and then increased through the minimum. The variation of A2 and <s2> from light scattering with the concentration of H2SO4 has the same tendency as that of the intrinsic viscosity ([η]).
  • Awadhesh Kumar, Rajesh Kumar Vatsa, Pradyot Kumar Chowdhury, Kuchimanc ...
    Type: Accounts
    Subject area: AI
    1993 Volume 66 Issue 6 Pages 1603-1607
    Published: 1993
    Released: August 07, 2006
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    The pulsed CO2 laser induced SF6 sensitized photodissociation of bromocyclobutane (BCB) and cyclohexene (CHN) is investigated. BCB has two dissociation channels from its ground electronic state, HBr elimination yielding 1,3-butadiene is the major channel (>90%) whereas, the ring cleavage producing vinyl bromide and ethylene is the minor one. The time-resolved formation of 1,3-butadiene is monitored by UV absorption from which unimolecular rate constants for BCB and CHN dissociation are found to be 8 × 105 s−1 and 1 × 106 s−1, respectively. A red-shift of 38 nm and 50 nm observed in the UV spectra of butadiene produced respectively from BCB and CHN, suggests that vibrationally hot butadiene molecules are formed. The effects of laser fluence, pressure of SF6 and the no. of laser pulses on dissociation yield and the branching ratio in BCB are also investigated.
  • Yukio Sasaki, Ken-ichi Miyagawa, Nobuyuki Wataru, Hideki Kaido
    1993 Volume 66 Issue 6 Pages 1608-1612
    Published: 1993
    Released: August 07, 2006
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    The physical properties of binary mixtures of 3-propylsydnone (3-PSD)–tetrahydrofuran (THF) and 1,2-dimethoxyethane (DME) at various temperatures were investigated in terms of the dielectric constant (ε), refractive index (nD), density (ρ), and viscosity (η) measurements. The dielectric constants of these binary mixtures gradually decrease with increasing THF and DME mole fractions (XTHF and XDME). The dielectric constant data can be described by a cubic equation of the THF and DME mole fractions. The nD of these binary mixtures decreases linearly with increasing temperature. A linear relationship exists between the density and the temperature at each XTHF and XDME. The η of these binary mixtures rapidly decrease with increasing XTHF and XDME at low temperature. The excess viscosity (ηE) of the mixtures is negative over the entire THF and DME mole fractions, and has a maximum value at 0.4 XTHF and XDME. The negative value of ηE may be taken as the formation of weakly associated compounds. It was found from the 1H and 17O NMR spectra that the interaction in a 3-PSD–THF mixture occurs highly between the hydrogen of the 4-position in the sydnone ring and the oxygen of the THF molecule. From the ηE and NMR spectra it seems that one of the associated compounds due to weak hydrogen bonding in these binary mixtures is formed at the 0.4 THF and DME mole fractions. The interactions in these binary mixtures were investigated on the basis of the activation parameters by using the Eyring rate equation. The activation enthalpy (ΔHη*) gradually increases with increasing viscosity of the mixtures. It is considered that the mechanism of viscous flow for these binary mixtures is a thermally activated single process. The activation entropy (ΔSη*) gradually changes from positive to negative with increasing XTHF and XDME. It seems that the change of sign in ΔSη* near to 0.4 THF and DME mole fractions depends on the formation of weakly associated compounds at that mole fraction. The activation Gibbs energy (ΔGη*) with a positive ΔSη* value gradually decreases with increasing temperature. On the contrary, the ΔGη* with a negative ΔSη* value gradually increases with increasing temperature. This means that the change in ΔSη* greatly contributes to that of ΔGη*.
  • Kohsuke Fukushima, Masayuki Someya, Ryosuke Shimozawa
    1993 Volume 66 Issue 6 Pages 1613-1617
    Published: 1993
    Released: August 07, 2006
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    Binding isotherms of a local anesthetic, dibucaine, to phospholipid vesicles were measured using a dialysis method. Two types of phospholipids, dilauroylphosphatidic acid (DLPA) and dilauroylphosphatidylcholine (DLPC), were used to prepare vesicles. The binding isotherms for pure DLPA and DLPC vesicles and their mixtures were analyzed with the Hill equation. The binding parameters obtained for pure phospholipid vesicles reproduce the binding isotherms for the mixed vesicles by taking account of the mixing ratio; this indicates the presence of independent binding sites, corresponding to the DLPA and DLPC molecule, in the mixed vesicle.
  • Iwao Satake, Tomoko Fukunaga, Tamaki Maeda, Yuko Soeda, Katumitu Hayak ...
    Type: Accounts
    Subject area: AI
    1993 Volume 66 Issue 6 Pages 1618-1621
    Published: 1993
    Released: August 07, 2006
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    The micellar properties of α,ω-alkanediammonium bis(dodecyl sulfate) with hydrocarbon chain length (n) from 3 to 6 were studied by conductivity, surfactant ion activity, and fluorescence quenching measurements. The critical micelle concentration (CMC) decreases gradually with increasing n in such a way that ln CMC vs. n plot gives a straight line above n = 3. The binding degree of counterion head group to the micelle remains virtually constant of 0.95 regardless of n studied. The estimated value of −0.36 kT for the transfer free energy per methylene group of counterion from aqueous to micellar environments suggests that the hydrocarbon part of the counterion participates in the weak hydrophobic interaction with micellar core. Although the micelle aggregation number is always larger than those of bivalent metal dodecyl sulfates, it tends to decrease as n increases.
  • Tomohiro Oshiyama, Ohgi Takahashi, Kenji Morihashi, Osamu Kikuchi, Kat ...
    1993 Volume 66 Issue 6 Pages 1622-1626
    Published: 1993
    Released: August 07, 2006
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    Ab initio and AM1 multi-reference SCI calculations have been applied to the stilbene cation radical and the potential energy curves for the lower doublet states were obtained as a function of the twist angle about the central C–C bond to elucidate the photochemical cis–trans isomerization process. The shape of the calculated potential energy curves has suggested that the cis→trans one-way isomerization proceeds very efficiently from an upper excited state of the cis-stilbene cation radical.
  • Shigeya Niizuma, Hiroki Kawata
    1993 Volume 66 Issue 6 Pages 1627-1632
    Published: 1993
    Released: August 07, 2006
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    The photoreaction of the solution systems of 9-acridone (or N-methyl-9-acridone) and phenols was investigated by optical spectroscopy, ESR, and time-resolved CIDEP techniques. CIDEP signals of acridone semiquinone and phenoxyl radicals were detected together and the hyperfine coupling constants of acridone semiquinone were determined for the first time by simulation method. It was also clarified that radical pair mechanism (RPM) with triplet precursor and triplet mechanism (TM) were the main spin polarization mechanisms in these systems. The results indicate that the excited triplet state of acridone abstracts a hydrogen of phenols. Temperature, phenol concentration, light intensity and time dependence of the phenoxyl CIDEP signal intensity and/or pattern supported the conclusion.
  • Tsugitoshi Ogura, Masazumi Tanoura, Akio Hiraki
    1993 Volume 66 Issue 6 Pages 1633-1639
    Published: 1993
    Released: August 07, 2006
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    The roles and behaviors of an anionic surfactant, such as naphthalenesulfonate-formaldehyde condensate (NSF) and poly(styrenesulfonate) (PSS) in the high-loaded suspensions of the Celejon coal with low mineral content (1.2%), carbon black, kaolinite, and montmorillonite were studied. It was found that it is necessary to prepare a slurry of low-viscosity Celejon coal, carbon black and kaolinite in such a way that the surfactant is present as saturatedly adsorbed on the particles as well as being free in water. In the presence of a surfactant, high-loaded suspensions exhibited non-Newtonian fluidity without yield values in their shear-rate and shear stress relation. In contrast, neither NSF nor PSS showed any adsorption on the bentonite particles. Its suspension exhibited a non-Newtonian fluidity with the yield value, even if its concentration was low. The roles of the bentonite were confirmed by adding bentonite to the CWM of Celejon. The CWM of Taiheiyo coal which carried 4.81% montmorillonite suffered a limited coal concentration due to because of a large yield value. Sodium polycarbonate was found to be effective to reduce the yield value, allowing a high coal concentration in CWM.
  • Teruyuki Komatsu, Shin-ichi Kumamoto, Hiroyuki Nishide, Eishun Tsuchid ...
    1993 Volume 66 Issue 6 Pages 1640-1646
    Published: 1993
    Released: August 07, 2006
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    New double-sided porphyrinatoiron(II) complexes having a polar cavity which includes an amide moiety (5,10,15-tris[2,6-bis(3,3-dimethylbutyryloxy)phenyl]-20-[2-[N-acetylvalyloxy]-6-(3,3-dimethylbutyryloxy)phenyl]porphinatoiron(II) (1b) and 5,10,15-tris[2,6-bis(3,3-dimethylbutyryloxy)phenyl]-20-[2-[3,5-bis(acetamido)benzoyloxy]-6-(3,3-dimethylbutyryloxy)phenyl]porphinatoiron(II) (2b)) were synthesized. 1H NMR spectroscopy indicated that the amide residues are located on the porphyrin ring plane. The O2 and CO binding affinities of 1b and 2b were higher than those of 5,10,15,20-tetrakis[2,6-bis(3,3-dimethylbutyryloxy)phenyl]porphinatoiron(II) (4b), in response to the local polarity in the cavity. The polar amide residue resulted in a decreased O2 dissociation rate. Thermodynamic parameters for the gaseous ligand bindings to the 2b complex were also determined.
  • Junji Noro, Tatsuya Sekine
    Type: Accounts
    Subject area: AI
    1993 Volume 66 Issue 6 Pages 1647-1651
    Published: 1993
    Released: August 07, 2006
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    The solvent extractions of europium(III) in 0.1 mol dm−3 sodium nitrate solutions with acetylacetone (Hacac), benzoylacetone (Hbza), benzoyltrifluoroacetone (Hbfa), trifluoroacetylacetone (Htfa), and hexafluoroacetylacetone (Hhfa) into chloroform were measured in both the absence and presence of tetrabutylammonium (tba+). From the results and those with 2-thenoyltrifluoroacetone (Htta) in a previous study it was concluded that extractions with the CF3– containing β-diketones, Hbfa, Htfa, Hhfa, and Htta are greatly enhanced by the addition of tba+. This could be explained in terms of the extraction of a ternary complex, EuA4 tba+ (A is a β-diketonate ion). However, extractions with Hacac and Hbza were nearly the same when tba+ was added. The enhancement of extraction was statistically treated by assuming an association of EuA3 and Atba+ in the organic phase. The equilibrium constants for an association with different β-diketones were compared, and the reasons for the difference in the association equilibrium as well as the enhancement of extraction are described.
  • Haruo Sekizaki, Eiko Toyota, Yoshihisa Yamamoto
    Type: Accounts
    Subject area: AI
    1993 Volume 66 Issue 6 Pages 1652-1657
    Published: 1993
    Released: August 07, 2006
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    The structure of the cis-α-salicylato(triethylenetetramine)cobalt(III) ion was confirmed by an X-ray crystallographic analysis. The conformation of the triethylenetetramine part of this complex was slightly different from the cis-α-glycinato(triethylenetetramine)cobalt(III) ion. A comparison of the stability of the this cis-α-salicylato complex with that of the cis-α-glycinato complex on the cation-exchange resin and in water, respectively, are described. The signals of the 1H NMR and 13C NMR spectra were assigned based on the crystal structure.
  • Hiroshi Tomizawa, Kazumasa Harada, Eiichi Miki, Kunihiko Mizumachi, Ta ...
    Type: Accounts
    Subject area: AI
    1993 Volume 66 Issue 6 Pages 1658-1663
    Published: 1993
    Released: August 07, 2006
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    A mixture of mer- and fac-[RuCl3(en)NO], and mer-[RuX3(en)NO] (X = Br or I) were prepared from the corresponding [RuX5NO]2− (X = Cl, Br, or I) or hydrous RuX3·NO (X = Cl or Br) and en·2HX (en = ethylenediamine; X = Cl or Br). The crystal and molecular structures of mer-[RuX3(en)NO] (X = Cl, Br, or I) were determined by X-ray diffraction. The crystals were isomorphous; triclinic, with space group P1. The final R values were 0.0411 for [RuCl3(en)NO], 0.0271 for [RuBr3(en)NO], and 0.0535 for [RuI3(en)NO]. In these complexes, the three halogeno atoms were in the meridional arrangement and in a position cis to the NO. In all of the mer-complexes, the trans-strengthening effect which is expected to be caused by the NO was not observed for the Ru–N(en) bond. The synthesized complexes were also characterized by IR and NMR spectra.
  • Yasuaki Okamoto, Kiyoshi Hayashi, Yukihiro Kawahara, Takahiro Kumamaru
    Type: Accounts
    Subject area: AI
    1993 Volume 66 Issue 6 Pages 1664-1668
    Published: 1993
    Released: August 07, 2006
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    Electrodialysis pretreatment system was combined with a new dual cation-selective membrane tubes and was employed to reduce the basicity of the strongly basic sample solution prior to the ion chromatographic determination of halide ions by using a sodium salicylate solution as eluent. By using this system, large amount of cations such as sodium and potassium ions could also be removed from the sample solution through the membrane. The detection limits were 9.7, 5.4, 22.7, and 163 ng cm−3 and relative standard deviations at 0.5 μg cm−3 were 1.7, 1.2, 2.4, and 14% for fluoride, chloride, bromide, and iodide ions, respectively. Analytical results are given for rock samples fused with sodium hydroxide as a flux and afterward dissolved in water which shows strong basicity.
  • Jun Nishimoto, Akira Hironaka, Etsuro Iwamoto, Takahiro Kumamaru
    Type: Accounts
    Subject area: AI
    1993 Volume 66 Issue 6 Pages 1669-1674
    Published: 1993
    Released: August 07, 2006
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    The axial coordination of pyridine, 2-methylpyridine, 4-methylpyridine and water (W) hydrogen-bonded to each donor solvent (S) to the (1R,4S,8R,11S)-1,4,8,11-tetramethyl-1,4,8,11-tetraazacyclotetradecanenickel(II) cation ([Ni(tmc)]2+) in nitrobenzene has been investigated spectrophotometrically. Pyridine and its derivatives are hardly coordinated to [Ni(tmc)]2+ owing to steric hindrance, but the water which is hydrogen-bonded to the donor solvent as a 1 : 1 complex (WS) can be easily coordinated to form the five coordinated [Ni(tmc)(WS)]2+ cation with a coordination constant (KMWS in dm3 mol−1) of 6.5 for pyridine, 5.7 for 2-methylpyridine, and 11.5 for 4-methylpyridine. The smaller KMWS value for 2-methylpyridine is due to steric hindrance. It was found that the residual hydrogen atom of the coordinated water in WS can be hydrogen-bonded to further species such as S and WS to form additional kinds of five-coordinated complexes, [Ni(tmc)(WS–S)]2+ and [Ni(tmc)(WS–WS)]2+. Coordination of the doubly hydrogen-bonded water (WS–S) which is induced as a result is stronger for 4-methylpyridine than for pyridine. This reflects the substituent effect of 4-methyl group on the basicity. The basicity of pyridine and its derivatives has been discussed in connection with the electrostatic/charge-transfer balance for hydrogen-bonding, compared with dimethyl sulfoxide.
  • Masahiro Mikuriya, Toshinori Fujii, Tadashi Tokii, Asako Kawamori
    Type: Accounts
    Subject area: AI
    1993 Volume 66 Issue 6 Pages 1675-1686
    Published: 1993
    Released: August 07, 2006
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    Mononuclear and dinuclear manganese complexes with2,6-bis[N-(2-pyridylethyl)iminomethyl]-4-methylphenol (HL), [MnII2(L)(CH3COO)2(CH3OH)](ClO4) (1), [MnII2(L)(CH3COO)2(NCS)] (2), [MnII(HL)(NCS)2(H2O)] (3), [MnIIMnIII(L)(CH3COO)2(CH3OH)2](ClO4)2 (4), [MnIIMnIII(L)(CH3COO)2(NCS)2] (5), [MnIIMnIII(L)(CH3COO)2(N3)2]·2CH3OH (6), and [MnIII(HL)(N3)3] (7), have been prepared and characterized by infrared, electronic, and ESR spectra, as well as the temperature dependence of the magnetic susceptibilities (80—300 K). The molecular structures of 1, 2, 3, 6, and 7 were determined by single-crystal X-ray structure analyses. Complexes 1 and 2 have a μ-phenoxo-di-μ-acetato-bridged dinuclear structure, in which one manganese atom is five-coordinated and the other six-coordinated. Complex 6 is a μ-phenoxo-di-μ-acetato-bridged dinuclear molecule comprising an octahedral Mn(II) atom and an elongated-octahedral Mn(III) atom. The manganese atoms of 3 and 7 are six-coordinated in a distorted octahedral environment. The spectral and magnetic properties are discussed in relation to the crystal structures.
  • Masakazu Kita, Kazuhiro Nemoto, Kazuo Kashiwabara, Junnosuke Fujita, M ...
    Type: Accounts
    Subject area: AI
    1993 Volume 66 Issue 6 Pages 1687-1692
    Published: 1993
    Released: August 07, 2006
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    The structures of [Co(acac)2{(CH3)2XCH2CH2NH2}]ClO4 (acac = 2,4–pentanedionate ion, X = N (complex 1), P (complex 2), and As (complex 3)) with a series of group 15 donor atoms were determined by the single-crystal X-ray diffraction method. Crystal data and final R values are: for 1, orthorhombic, Pba2, a = 13.192(2), b = 25.504(5), c = 11.840(2) Å, V = 3984(1) Å3, Dm = 1.47(2), Dx = 1.48 g cm−3 and Z = 8, R = 0.050 for 2684 reflections. For 2, monoclinic, P21/c, a = 13.953(6), b = 25.061(10), c = 12.079(7) Å, β = 92.29(6)°, V = 4220(2) Å3, Dm = 1.45(3), Dx = 1.45 g cm−3, Z = 8, R = 0.084 for 5801 reflections. For 3, monoclinic, C2/c, a = 28.125(9), b = 13.303(1), c = 12.647(4) Å, β = 115.41(4)°, V = 4274(2) Å3, Dm = 1.50(3), Dx = 1.54 g cm−3, Z = 8, R = 0.051 for 3698 reflections. All the complex ions have a similar structure, forming a distorted octahedron with 4O, N, and X donor atoms. The Co–X bond lengths are av. 2.026(8) Å for 1, av. 2.192(3) Å for 2, and 2.302(1) Å for 3. The Co–O bond lengths trans to X are av. 1.886(6) Å for 1, av. 1.950(5) Å for 2, and 1.928(3) Å for 3, which are longer by 0.002(6), 0.065(6) and 0.037(4) Å, respectively, than the average lengths of other three Co–O bonds (1: av. 1.884(6), 2: av. 1.885(6), 3: 1.891(4) Å).
  • Kohji Maeda, Sadayuki Himeno, Atsuyoshi Saito, Toshitaka Hori
    Type: Accounts
    Subject area: AI
    1993 Volume 66 Issue 6 Pages 1693-1698
    Published: 1993
    Released: August 07, 2006
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    A green 11-molybdoarsenite(III) complex, which was formed in an Mo(VI)–AsO33−–HCl–CH3CN system at room temperature, was isolated as the tetrabutylammonium (n-Bu4N+) salt, being characterized by its voltammetric behavior and its IR and UV-visible spectra. The heteropolyanion undergoes two-step one-electron reductions in CH3CN and three-step two-electron reductions in acidified CH3CN. The electrochemical reduction produces mixed-valence blue species at the glassy carbon (GC) electrode. The formation conditions and chemical properties were compared with those of 12-molybdoarsenate(V) with the Keggin structure. The presence of water-miscible organic solvents like CH3CN and CH3COCH3 is absolutely necessary for the formation of the green heteropolyanion.
  • Hideyuki Kuno, Makoto Shibagaki, Kyoko Takahashi, Hajime Matsushita
    1993 Volume 66 Issue 6 Pages 1699-1702
    Published: 1993
    Released: August 07, 2006
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    A modified catalyst was prepared by the reaction of trimethylsilyl chloride and hydrous zirconium(IV) oxide. It was then applied to the oxidation of alcohols by using carbonyl compounds as hydrogen acceptors. In the case of cycloalkanols, the oxidation proceeded efficiently to give the corresponding ketones. Further, primary aliphatic alcohols were converted to the corresponding aldehydes in high yields in a batch reaction system. In addition, it was investigated that the oxidation was influenced by a variety of solvents and hydrogen acceptors.
  • Shiv Pratap Singh, Jitander Kumar Kapoor, Devinder Kumar
    1993 Volume 66 Issue 6 Pages 1703-1706
    Published: 1993
    Released: August 07, 2006
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    Reaction of several hydrazinobenzoquinolines with 1,3-diketones affords pyrazolylbenzoquinolines rather than the reported benzodiazepinoquinolines. The structural assignment is based upon NMR (1H and 13C) spectral data and an unambiguous synthesis.
  • J. Retuert, M. Yazdani- Pedram, F. Martínez, M. Jeria
    1993 Volume 66 Issue 6 Pages 1707-1708
    Published: 1993
    Released: August 07, 2006
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    A method of obtaining soluble itaconic acid (IA)–ethylene glycol (EG) unsaturated polyesters was developed. The reaction between IA and EG was conducted under moderate vacuum (50—60 mmHg) at 120 °C and stopped by nearly 85% conversion to avoid crosslinking. No isomerization of itaconate to citraconate and/or mesaconate was observed. The residual double bond contained in the polyester resin showed to be highly reactive and promoted gelification after few days. Therefore copolymerization reactions of the resin with a variety of vinyl monomers proceed without radical initiator. The synthetic method was successfully applied to reactions of IA with other glycols.
  • Masao Shiozaki, Masami Arai, Tetsuo Hiraoka, Masahiro Nishijima, Yuzur ...
    Type: Accounts
    Subject area: AI
    1993 Volume 66 Issue 6 Pages 1709-1713
    Published: 1993
    Released: August 07, 2006
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    2,3-Dideoxy-2-[(3R)-3-hydroxytetradecanoylamino]-3-C-[(3R)-(3-hydroxytetradecanoyloxy)methyl]-4-O-phosphono-D-mannopyranose was synthesized from (1R,2S,4S,5S)-6-(2,4-dimethoxybenzyl)-4-hydroxy-2-[(1R)-1,2-isopropyridenedioxyethyl]-3-oxa-6-azabicyclo[3.2.0]heptan-7-one.
  • Meng-Xin Ding, Akihiko Ishii, Juzo Nakayawa, Masamatsu Hoshino
    1993 Volume 66 Issue 6 Pages 1714-1721
    Published: 1993
    Released: August 07, 2006
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    The reactions of 2,2,4,4-tetramethyl-1,5-diphenyl-1,5-pentanedione monohydrazone with S2Cl2 and Se2Cl2 gave 2,2,4,4-tetramethyl-1,5-diphenyl-8-oxa-6,7-dithiabicyclo[3.2.1]octane (9) and 2,2,4,4-tetramethyl-1,5-diphenyl-8-oxa-6,7-diselenabicyclo[3.2.1]octane (10), respectively. Dechalcogenation of 9 or 10 with triphenylphosphine in boiling toluene yielded an equilibrium mixture of 2,2,4,4-tetramethyl-1,5-diphenyl-6-oxa-7-thiabicyclo[3.1.1]heptane (11) and 2,2,4,4-tetramethyl-1,5-diphenyl-5-thioxo-1-pentanone (13) or 2,2,4,4-tetramethyl-1,5-diphenyl-6-oxa-7-selenabicyclo[3.1.1]heptane (12), respectively. On the other hand, the reaction of 10 with hexamethylphosphorous triamide [P(NMe2)3] in boiling toluene gave 12, 3-methyl-3-(2,2-dimethyl-3-oxo-3-phenylpropyl)-2-phenylselenetanes (18), 5-benzoyl-3,3,5-trimethy1-2-phenylselenanes (19), 6,6,8,8-tetramethyl-9-phenyl-6,7,8,9-tetrahydro-5H-benzocyclohepten-5-one (20), and 3,3,5,5-tetramethyl-1,2-diphenylcyclopentene (21), while that of 9 afforded 11, 13, 3-(2-benzoyl-2-methylpropyl)-3-methyl-2-phenylthietanes, 20, and 21. The reaction of 12 with P(NMe2)3 also gave 18, 19, 20, and 21. A single-electron transfer mechanism seems to be operative in the reaction of 9 or 10 with P(NMe2)3. Compounds 11 and 13 are in equilibrium with each other at room temperature, while a ring-opening of 12 to 2,2,4,4-tetramethyl-1,5-diphenyl-5-selenoxo-1-pentanone is observed on heating by the UV-vis and 1H NMR spectra.
  • Fathy Mohamed Abdelrazek, Abdellatif Mohamed Salah
    Type: Accounts
    Subject area: AI
    1993 Volume 66 Issue 6 Pages 1722-1726
    Published: 1993
    Released: August 07, 2006
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    α-(Thiocyanatomethyl)benzylidenemalononitrile undergoes azo coupling with diazotized aromatic amines (ArNH2) to afford azo derivatives. The azo derivatives (Ar = Ph, 4-MeC6H4, 4-ClC6H4, 4-MeOC6H4) were readily cyclized on reflux in aqueous NaOH to 3(2H)-pyridazinimine derivatives. These latter compounds were transformed into the corresponding pyrrole derivatives on reflux in glacial acetic acid with Zn dust presumably via reductive cleavage of the N–N bond followed by recyclization with loss of ammonia. Under similar conditions the azo derivative (Ar = 2-NCC6H4) was cyclized into 6H-pyridazino[3,2-a]quinazolin-6-imine derivative which was easily transformed into the 6H-pyridazino[3,2-a]quinazolin-6-one on reflux in ethanolic HCl. This last compound was also obtained from the azo derivatives (Ar = 2-HOOCC6H4 and 2-MeOOCC6H4) by reflux in aq NaOH. The starting benzylidenemalononitrile reacts also with arylmethyleneamalononitrile or ethyl arylmethylenecyanoacetate (aryl = Ph, furyl, or thienyl) to afford substituted benzonitrile derivatives.
  • Tomomi Kinoshita, Koichi Shibayama, Masaaki Itoh, Ken’ichi Takeu ...
    Type: Accounts
    Subject area: AI
    1993 Volume 66 Issue 6 Pages 1727-1731
    Published: 1993
    Released: August 07, 2006
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    The solvolysis of 2,2-dimethyl-1-(p-methoxyphenyl)propyl p-nitrobenzoate in phenol provides a novel example of the common ion salt effect (rate depression) which arises at the stage of the second ion pair intermediate (Int-2; the rear-side shielded ion pair intermediate), not the dissociated (free) carbocation intermediate as generally supposed so far. This example demonstrates that “the common ion rate depression” could not give evidence for the intermediacy of the dissociated carbocation intermediate in the SN1 solvolysis, but an indicator for the stability of solvolysis intermediates including the ion pair intermediate.
  • Yoshito Takeuchi, Ieva Zicmane, Georges Manuel, Rabah Boukherroub
    1993 Volume 66 Issue 6 Pages 1732-1737
    Published: 1993
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    73Ge and 13C NMR spectra of several 3-germabicyclo[3.1.0]hexanes (GBCH) were determined. The results are consistent with the structure as predicted by molecular mechanics calculations. Thus, GBCH prefer the boat form as bicyclo[3.1.0]hexanes (BCH) do. GBCH finally assumes the chair form by excessive substitution.
  • Hidenori Chikashita, Kiyoharu Hirao, Kazuyoshi Itoh
    Type: Accounts
    Subject area: AI
    1993 Volume 66 Issue 6 Pages 1738-1742
    Published: 1993
    Released: August 07, 2006
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    The stereoselective asymmetric synthesis of two trans isomers of the title natural product, (3R,6R)- and (3S,6S)-tetrahydro-2,2,6-trimethyl-2H-pyran-3-ol, was achieved by starting with easily obtainable ethyl (S)-3-hydroxybutanoate, via the stereospecific asymmetric construction of substituted tetrahydropyran skeletons by the one-step cyclodehydration process of dithioacetal-functionalized chiral 1,5-diols with PPh3 and diethyl azodicarboxylate in THF at room temperature.
  • Haruo Matsuyama, Sana Fujii, Yoshihiro Nakamura, Koichi Kikuchi, Isao ...
    Type: Accounts
    Subject area: AI
    1993 Volume 66 Issue 6 Pages 1743-1753
    Published: 1993
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    The Optically active 3,3-dialkyl-4-thianones 3 and 4 were prepared in moderate yields with about 90% enantiomeric purity using an asymmetric process involving a Michael-type alkylation of chiral 3-alkyl-4-thianimines with methyl vinyl ketone or methyl acrylate. The diketones 3 were then transformed into new heterocycles 5 by base-induced cyclization. 3-Methyl- and 3-allyl-3-(2-methoxycarbonylethyl)-4-thianone ((+)-4a and (+)-4b) were converted into the bicyclic lactones (−)-6 and (−)-7, respectively. The stereochemistry of the sulfone (+)-8 derived from the lactone (−)-6a was determined by a X-ray crystal structure analysis. Desulfurization of the lactone (−)-6b using nickel boride afforded the corresponding lactone (+)-9. A synthesis of optically active 2-alkyl-2-methyl-3-cyclopentenone (S)-(+)-15 via the Ramberg–Bäcklund reaction from the keto ester (R)-(+)-4a was also accomplished.
  • Norio Yoshino, Yasushi Yamamoto, Katsumi Hamano, Tokuzo Kawase
    1993 Volume 66 Issue 6 Pages 1754-1758
    Published: 1993
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    Four silane coupling agents, (1H,1H,2H,2H-polyfluoroalkyl)trimethoxysilanes ((1H,1H,2H,2H-henicosafluorododecyl)trimethoxysilane, C10F21C2H4Si(OCH3)3, (1H,1H,2H,2H-heptadecafluorodecyl)trimethoxysilane, C8F17C2H4Si(OCH3)3, (1H,1H,2H,2H-tridecafluorooctyl)trimethoxysilane, C6F13C2H4Si(OCH3)3, and (1H,1H,2H,2H-nonafluorohexyl)trimethoxysilane, C4F9C2H4Si(OCH3)3), were prepared by the hydrosilylation of trichlorosilane with the corresponding 1H,1H,2H-polyfluoro-1-alkene in the presence of hydrogen hexachloroplatinate(IV), followed by reaction with sodium methoxide. The surface modification of glass plate was attempted using these products. From measurements of the contact angles θ (°) of water and oleic acid against a modified glass plate surface, the coupling agents were found to have high modification ability. The modification produced a glass surface with high oxidation resistance.
  • Masakazu Yamashita, Kaoru Matsumiya, Ken-ichi Nakano
    Type: Accounts
    Subject area: AI
    1993 Volume 66 Issue 6 Pages 1759-1763
    Published: 1993
    Released: August 07, 2006
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    Lithiated α,β-unsaturated aldehyde N,N-dimethylhydrazones reacted with alkyl halides accompanied by double bond migration to give α-alkylated β,γ-unsaturated aldehyde N,N-dimethylhydrazones in satisfactory yields. This reaction was found to be caused at the first step by deprotonation from a γ-carbon atom by lithium diisopropylamide. In the case of hydrazones with two kinds of γ-protons, deprotonation from the less hindered γ-carbon occurred selectively. Using this reaction, a novel sesquiterpene, 2,5,9-trimethyl-2-vinyl-4,8-decadienal, which has a vinyl group at the α-position, was synthesized in a good yield.
  • Masato Nanasawa, Makoto Kaneko, Hiroyoshi Kamogawa
    1993 Volume 66 Issue 6 Pages 1764-1767
    Published: 1993
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    Viologen metal complexes comprising 2,2′- and 4,4′-bipyridinium hexacyanoferrate(II) were synthesized starting from the corresponding halides by an anion-exchange reaction. The charge-transfer bands appeared in aqueous solutions, whereas radical cation peaks in visible region appeared in solid polymer matrices via a photoinduced electron transfer within the viologen molecule; their absorptions were dependent upon both the kind of bipyridinium dication and the media, such as the solvents and polymer matrices. The reversible redox reaction by photon mode (color development) and by heat mode (bleaching) can be repeated in the absence of atmospheric oxygen.
  • Hitoshi Tamiaki, Ayumu Kiyomori, Kazuhiro Maruyama
    Type: Accounts
    Subject area: AI
    1993 Volume 66 Issue 6 Pages 1768-1772
    Published: 1993
    Released: August 07, 2006
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    Several benzophenone-β-turned dipeptide-alkyl chain molecules were prepared. In acetonitrile, intramolecular photochemical reaction of the synthetic molecules was investigated. The photoexcited benzophenone moiety abstracted selectively a hydrogen of the alkyl chain in the molecule. Such a site selectivity showed that the β-turned conformation might be rigid enough for the hydrogen abstraction in the excited state.
  • Harald Müller, Yoshinobu Ueba
    Type: Accounts
    Subject area: AI
    1993 Volume 66 Issue 6 Pages 1773-1777
    Published: 1993
    Released: August 07, 2006
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    Bis[oxybis(methylenethio)]tetrathiafulvalene (BOBMT-TTF) and bis[thiobis(methylenethio)]tetrathiafulvalene (BTBMT-TTF) were synthesized in two steps starting from 1,3,4,6-tetrathiapentalene-2,5-dione. The electrochemical and donor properties of both compounds are discussed. BOBMT-TTF forms a highly conducting charge transfer complex with TCNQ (σRT 10 S cm−1).
  • Masatoshi Motoi, Kunimasa Noguchi, Akio Arano, Shigeyoshi Kanoh, Akihi ...
    1993 Volume 66 Issue 6 Pages 1778-1789
    Published: 1993
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    Several oxetane derivatives carrying the azobenzene moiety at the C-3 position of the oxetane ring through the spacer arms of differing lengths were prepared by a substitution reaction of the corresponding bromide or p-toluenesulfonate residue of the oxetane with 4-hydroxyazobenzenes. The polymers of these oxetane derivatives were readily obtained by cationic ring-opening polymerization using the adequately increased amount of a THF· BF3 complex as an initiator at 20—30 °C. The liquid crystalline property of the polymers thus obtained were examined by differential scanning calorimetry and by optical polarized microscopy. From these measurements the influences of the p′-substituted azobenzene and of the spacer arm on the liquid crystalline property were found.
  • Masaki Matsui, Bharati Joglekar, Yoshinao Ishigure, Katsuyoshi Shibata ...
    1993 Volume 66 Issue 6 Pages 1790-1794
    Published: 1993
    Released: August 07, 2006
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    New fluorine-containing azopyridone dyes, 3-cyano-6-hydroxy-5-[2-(perfluoroalkyl)phenylazo]-2-pyridones, have been synthesized. Though the introduction of a long perfluoroalkyl group lowered film forming ability and sensitivity, 5-[2-(trifluoromethyl)phenylazo]- and 5-[2-(perfluorobutyl)phenylazo]-3-cyano-4-methyl-6-hydroxy-2-pyridones showed good photostability.
  • Joji Ohshita, Hiroshi Ohsaki, Mitsuo Ishikawa
    1993 Volume 66 Issue 6 Pages 1795-1798
    Published: 1993
    Released: August 07, 2006
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    Poly[(1,2-dimethyl-1,2-diphenyl-1,2-disilanylene)-1,4-naphthylene], poly[(1,2-dimethyl-1,2-diphenyl-1,2-disilanylene)-1,5-naphthylene], poly[(1,2-dimethyl-1,2-diphenyl-1,2-disilanylene)-2,6-naphthylene], and poly[(1,2-dimethyl-1,2-diphenyl-1,2-disilanylene)-2,7-naphthylene] were synthesized by the condensation reaction of the corresponding bis(chloromethylphenylsilyl)naphthalenes with sodium. Photochemical properties of these polymers have been reported.
  • Nobutsugu Yamagata, Kouji Igarashi, Hiroki Saitoh, Susumu Okazaki
    Type: Accounts
    Subject area: AI
    1993 Volume 66 Issue 6 Pages 1799-1806
    Published: 1993
    Released: August 07, 2006
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    A voluminous composite oxide of BaLa2O4 was prepared by kneading powders of Ba(OH)2·8H2O (A) and La(NO3)3·6H2O (B) with a small amount of water, followed by pyrolysis at 1100 °C. The resulting material (apparent volume of ca. 3 cm3 g−1) was found to be effective as a catalyst for the oxidative coupling of methane to ethane and ethylene. The preparative conditions of the voluminous BaLa2O4 catalyst and these effects on the C2 formation were investigated. When reagents A and B were mixed with each other at 33 atom-% Ba and then calcined for 10 min at 1100 °C, the BaLa2O4 composite oxide was most advantageously produced and a high C2 yield of ca. 19% was reproducibly obtained over a non-pressed or voluminous catalyst. The high surface basicity and macro-porous structure of the voluminous BaLa2O4 catalyst, which were responsible for its high C2 yield, are discussed.
  • Naoji Kubota
    1993 Volume 66 Issue 6 Pages 1807-1812
    Published: 1993
    Released: August 07, 2006
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    Chitosan was treated with NaBO3 under a homogeneous condition in which it was previously dissolved in an aqueous acetic acid solution. Different molecular weight chitosan samples were obtained, depending upon the reaction conditions, NaBO3 concentration, reaction temperature, and reaction time. The performance of chitosan hydrogel for use in a sustained-release drug was investigated while focusing on the swelling properties of chitosan coated on a drug. Theophylline was used as a model drug to be released. Theophylline tablets were coated with respective chitosan samples, and then tested for the drug release rate. Each drug release obeyed zero-order or near zero-order kinetics, due to a reservoir system comprising a saturated theophylline solution and a chitosan hydrogel wall. The release rate of theophylline decreased with increasing the amount of coated chitosan, which affects the permeability of the drug, and increased with decreasing the molecular weight of coated chitosan, which affects the degree of hydration of the gel. A lag time effect was observed when higher molecular weight chitosan was coated. These experimental results were interpreted in terms of the degree of hydration of chitosan hydrogel and Fick’s law of diffusion.
  • Guo-ding Zhou, Yiqi Feng, Yiping Wu, Takenori Notoya, Tatsuo Ishikawa
    Type: Accounts
    Subject area: AI
    1993 Volume 66 Issue 6 Pages 1813-1816
    Published: 1993
    Released: August 07, 2006
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    Corrosion inhibition of copper in a low-conductivity medium ( < 10 μS cm−1) containing benzotriazole (BTA) and/or 2-mercatobenzothiazole (MBT) was studied by using the AC impedance technique, Auger electron spectroscopy and corrosion tests. As the MBT concentration increased, the corrosion rate of copper abruptly rose to a peak, rapidly fell, and then finally decreased steadily. The maximum corrosion rate appeared at a MBT concentration of about 0.5 ppm. However, a concentration of more than 1.5 ppm MBT could effectively inhibit copper corrosion. The results from AC impedance measurements agreed with those from corrosion tests. The film resistance could be observed only when the MBT concentration was in excess of 1.5 ppm. A combination of BTA and MBT proved to be more effective than either compound used alone.
  • Yutaka Ikushima, Norio Saito, Masahiko Arai
    1993 Volume 66 Issue 6 Pages 1817-1819
    Published: 1993
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    The solvent polarity parameters, including the dipolarity/polarizability π* parameter, hydrogen-bond donor acidity α parameter, and hydrogen-bond acceptor basicity β parameter, were measured for supercritical carbon dioxide and cosolvent systems with ethanol, 2,2,2-trifluoroethanol, and dimethyl sulfoxide at pressures of 9.81—27.95 MPa and 318 K. A linear correlation was examined for relating those parameters with each other.
  • Kunio Fukushima, Hui Cheng He
    1993 Volume 66 Issue 6 Pages 1820-1821
    Published: 1993
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    The FT-IR spectra of a valeric acid–urea–water system and a 1-butanol–urea–water system were measured. By comparing the spectra with those of related systems, an inclusion structure of urea molecules was found to exist in the solution state; the interpretation that the increase in the solubility of valeric acid or 1-butanol into water by the addition of urea is due to the existence of an inclusion structure was verified.
  • Kenji Inagaki, Kimie Sawaki
    Type: Accounts
    Subject area: AI
    1993 Volume 66 Issue 6 Pages 1822-1825
    Published: 1993
    Released: August 07, 2006
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    Two adducts obtained from reactions of dinucleotide (d(GpG)) with 1R,3S-cyclohexanediamineplatinum(II) have been investigated on the basis of NMR spectroscopy. They were assigned as interbase cross-linked adducts being platinated at the N7 positions of the adjacent guanine bases. Both isomers differ with respect to the orientation of the cyclohexane ring toward the carbonyl group at the 6 position of the adjacent guanine bases. A conformational analysis of the cyclohexane ring is also described.
  • Akio Yuchi, Katsuhito Matsui, Tomosuke Ishizuki, Hiroko Wada
    Type: Accounts
    Subject area: AI
    1993 Volume 66 Issue 6 Pages 1826-1827
    Published: 1993
    Released: August 07, 2006
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    Cyclic voltammograms of the cobalt(III) complexes with sulfonated azo compounds indicated one quasi-reversible electrode process at the Pt or Au electrode at −0.3—0 V vs. SCE in aqueous solutions, which was assigned to a metal-centered redox reaction. The formal potentials are linearly correlated with the logarithmic protonation constants of the ligands.
  • Isamu Inamura, Kazutomo Uchida
    Type: Accounts
    Subject area: AI
    1993 Volume 66 Issue 6 Pages 1828-1829
    Published: 1993
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    Gel chromatography of chlorophyllin (Cu–Na salt) in water was compared with that in aqueous poly(N-vinylpyrrolidone) (PVP) solution. A shoulder at 430 nm in the absorption spectra, which was observed in all fractionated PVP solution system, is due to the monomer of chlorophyllin (Cu–Na salt). PVP tends to suppress aggregation of chlorophyllin (Cu–Na salt).
  • Colacot J. Thomas, Krishna K. Bhandary, Leonard M. Thomas, Sobha E. Se ...
    Type: Accounts
    Subject area: AI
    1993 Volume 66 Issue 6 Pages 1830-1833
    Published: 1993
    Released: August 07, 2006
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    A 1 : 2 mole reaction between S4N4 and diphenyl(2-pyridyl)phosphine has given (NC5H4)Ph2P=N–S3N3 in 70% yield. Crystals of (NC5H4)Ph2P=N–S3N3 are monoclinic, space group P21/n with a = 11.543(8), b = 13.254(9), c = 13.636(5) Å, β = 104.65(6)°, and Z = 4. The structure is refined to a final R value of 0.057 using 2916 reflections [I > 2σ (I)]. The S3N3 ring is stacked against one of the phenyl rings with an average SN distance of 1.61 Å.
  • Sachiko Yamada, Maki Kubo, Hiromi Fuke, Noriko Tsubaki, Koko Maeda
    Type: Accounts
    Subject area: AI
    1993 Volume 66 Issue 6 Pages 1834-1836
    Published: 1993
    Released: August 07, 2006
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    The photolysis of 10,10′-disubstituted 9,9′(10H,10′H)-biacridinylidenes afforded the corresponding 7,16-dihydrobenzo[1,2,3-kl:6,5,4-kl′]diacridines. The formation of photocyclized dihydrophenanthrene-type intermediates was confirmed spectroscopically.
  • Makoto Fujita, Jun Yazaki, Tadao Kuramochi, Katsuyuki Ogura
    1993 Volume 66 Issue 6 Pages 1837-1839
    Published: 1993
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    Reaction of a diphosphine ligand, bis[4-[2-(diphenylphosphino)ethyl]phenyl] ether (1) with Na2PdCl4 gave a macrocyclic dinuclear complex [PdCl2(μ-1)]2 (2) in a 58% isolated yield. The formation of 2 appears to result from a spontaneous self-assembly process under thermodynamic control, and thus, no special technique such as a high-dilution method was needed.
  • Yasuhiro Sato, Shunsuke Watanabe, Kenji Uneyama
    1993 Volume 66 Issue 6 Pages 1840-1843
    Published: 1993
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    Electrooxidation of trifluoroacetic acid in the presence of butyl acrylate in an MeCN–H2O–i-PrOH–(Pt) system under oxygen-bubbling provided a mixture of butyl 4,4,4-trifluoro-2-oxobutanoate and butyl 4,4,4-trifluoro-2-hydroxybutanoate.
  • Chung-gi Shin, Seiji Honda, Katsuhiro Morooka, Yasuchika Yonezawa
    Type: Accounts
    Subject area: AI
    1993 Volume 66 Issue 6 Pages 1844-1846
    Published: 1993
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    In order to further develop and expand the usefulness of N-carboxy-α-dehydroamino acid anhydride (ΔNCA), the optimum conditions of the acylation of ΔNCA with N-protected α-amino acids (AA) were thoroughly examined. Furthermore, various kinds of AA or dipeptides as a C-component were utilized in the acylation of ΔNCA, followed by condensation with an AA methyl ester as an N-component.
  • Anil Wali, Pralhad A. Ganeshpure, Sheo Satish
    1993 Volume 66 Issue 6 Pages 1847-1848
    Published: 1993
    Released: August 07, 2006
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    KMnO4 in acetonitrile–water has been found to be a convenient system for regenerating ketones from ketone oximes under mild conditions.
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