Chemistry Letters

cis–trans Isomerization of the Azobenzenes Included as Guests in Langmuir–Blodgett Films of Amphiphilic β-Cyclodextrin

Akira Yabe, Yasujiro Kawabata, Hiroyuki Niino, Motoo Tanaka, Akihiko O ...

1988 Volume 17 Issue 1 Pages 1-4
Published: January 05, 1988
Released on J-STAGE: March 27, 2006

DOIhttps://doi.org/10.1246/cl.1988.1

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Azobenzenes in the host–guest Langmuir–Blodgett films prepared with amphiphilic β-cyclodextrin and azobenzene derivatives showed a photochromic behavior with complete reversibility owing to the free volume of cyclodextrin cavity, whereas the trans-to-cis isomerization was restricted in the case of the pure LB film prepared with long-chain azobenzene derivative alone. Thermal cis-to-trans isomerizations in the LB films were also studied.

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Photochromism of [2.n]Metacyclophan-1-ene Derivatives

Shin-ichi Murakami, Tetsuo Tsutsui, Shogo Saito, Akira Miyazawa, Takeh ...

1988 Volume 17 Issue 1 Pages 5-8
Published: January 05, 1988
Released on J-STAGE: March 27, 2006

DOIhttps://doi.org/10.1246/cl.1988.5

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Photochromism of [2.n]metacyclophan-1-ene derivatives (n=2,3,4) was investigated. The reaction rates of the thermal decoloration were increased about thousand-fold with increasing of n by one.

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Improvement of Adsorption Capacity for Copper (II) Ion by N-Nonanoylation of Chitosan

Keisuke Kurita, Satoyuki Chikaoka, Yoshiyuki Koyama

1988 Volume 17 Issue 1 Pages 9-12
Published: January 05, 1988
Released on J-STAGE: March 27, 2006

DOIhttps://doi.org/10.1246/cl.1988.9

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Chitosan was selectively N-nonanoylated, and the influence of the long acyl groups on the adsorption of copper (II) ion was studied. The acylation with nonanoyl chloride was achieved efficiently on a highly swelled chitosan precipitate. The adsorption capacity could be improved markedly by a small extent of acylation.

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Polyion Complexation of Black Lipid Membranes (BLM) and Transport of a Hydrophobic Ion

Nobuyuki Higashi, Toyoki Kunitake, J. Möllerfeld, Helmut Ringsdor ...

1988 Volume 17 Issue 1 Pages 13-16
Published: January 05, 1988
Released on J-STAGE: March 27, 2006

DOIhttps://doi.org/10.1246/cl.1988.13

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Black lipid membranes were obtained from synthetic ammonium amphiphiles and their stabilities were enhanced by complexation with an anionic polymer. The permeation behavior of dipicrylamine anion was examined by the charge-pulse relaxation technique.

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Preparation of Hexafluoroacetone by Vapor Phase Oxidation Of Hexafluoropropene

Akito Kurosaki, Susumu Okazaki

1988 Volume 17 Issue 1 Pages 17-20
Published: January 05, 1988
Released on J-STAGE: March 27, 2006

DOIhttps://doi.org/10.1246/cl.1988.17

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Hexafluoroacetone was readily formed by circulating a gaseous mixture of hexafluoropropene and oxygen over platinum group metals supported on carbon. Reaction temperatures, ranging from 130 to 170 °C, gave both high selectivity and conversion for the hexafluoroacetone formation using a Pd/C catalyst.

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1,3-Asymmetric Induction in Acyclic Systems by Practical Application of Dithioacetal Group

Yutaka Honda, Eitaro Morita, Kimitaka Ohshiro, Gen-ichi Tsuchihashi

1988 Volume 17 Issue 1 Pages 21-24
Published: January 05, 1988
Released on J-STAGE: March 27, 2006

DOIhttps://doi.org/10.1246/cl.1988.21

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2-Lithio-2-(1-methyl-2-alkenyl)-1,3-dithianes showed 1,3-syn-selectivity on addition to aldehydes. Moreover this selectivity could be increased up to 97 %de by using equilibration of potassium alkoxide of the adduct in the presence of a ligand.

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Photopreparation of Heterogeneous Metathesis Catalysts from Metal Carbonyls Adsorbed on Solids

Yuji Wada, Chikanori Nakaoka, Akira Morikawa

1988 Volume 17 Issue 1 Pages 25-26
Published: January 05, 1988
Released on J-STAGE: March 27, 2006

DOIhttps://doi.org/10.1246/cl.1988.25

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It was demonstrated that Mo(CO)₆ and W(CO)₆ adsorbed on solid supports, such as porous Vycor glass and NaY zeolite, were photoactivated to be catalytically active for propene metathesis.

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Structure and Synthesis of Alboatrin, a Novel Phytotoxic Metabolite from Verticillium albo-atrum

Akitami Ichihara, Masahiko Nonaka, Sadao Sakamura, Rinzo Sato, Akitosh ...

1988 Volume 17 Issue 1 Pages 27-30
Published: January 05, 1988
Released on J-STAGE: March 27, 2006

DOIhttps://doi.org/10.1246/cl.1988.27

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Structure of Alboatrin, a novel phytotoxin isolated from Verticillium albo-atrum has been elucidated on the spectroscopic data and has been confirmed by the synthesis. A biogenesis for the unique phytotoxin is suggested.

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A New α-Iodination of Ketones Using Iodine–Cerium(IV) Ammonium Nitrate

C. Akira Horiuchi, Shinji Kiji

1988 Volume 17 Issue 1 Pages 31-34
Published: January 05, 1988
Released on J-STAGE: March 27, 2006

DOIhttps://doi.org/10.1246/cl.1988.31

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Direct α-iodination of some ketones using iodine–cerium(IV) ammonium nitrate in acetic acid or methanol, gave the corresponding α-iodoketone in high yield. In the case of 2-pentanone, 4-methyl-2-pentanone, 2-hexanone, and 2-heptanone in methanol, the regioselective products were obtained.

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Preparation and Structural Characterization of Binuclear Manganese(III) Complexes with 1,5-Bis(salicylideneamino)-3-pentanol and Its Derivatives

Masahiro Mikuriya, Sigeo Kida, Ichiro Murase

1988 Volume 17 Issue 1 Pages 35-38
Published: January 05, 1988
Released on J-STAGE: March 27, 2006

DOIhttps://doi.org/10.1246/cl.1988.35

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Three binuclear manganese(III) complexes with the title Schiff base ligands have been prepared and characterized. X-Ray structure analysis of [Mn₂(L_b) (CH₃O) (CH₃COO) (CH₃OH) (ClO₄)] (H₃L_b = 1,5-bis(5-chlorosalicylideneamino)-3-pentanol) has revealed that the two manganese ions are bridged by the alkoxide oxygen atom of the Schiff base ligand, the methoxide oxygen atom, and the oxygen atoms of the acetate ion with the Mn–Mn separation of 2.921(2) Å.

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Chemical Reactions in Medium Density Fluids. Inversion of Density Dependence of the Dimerization Equilibrium of 2-Methyl-2-nitrosopropane in Carbon Dioxide

Yoshifumi Kimura, Yosuke Yoshimura, Masaru Nakahara

1988 Volume 17 Issue 1 Pages 39-42
Published: January 05, 1988
Released on J-STAGE: March 27, 2006

DOIhttps://doi.org/10.1246/cl.1988.39

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Pressure effect on the dimerization–dissociation reaction of 2-methyl-2-nitrosopropane was studied in supercritical carbon dioxide. The configurational volume change for the dimerization, which was negative at high density, was found to be positive in a medium density region.

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Ion-pair Extraction of Gallium(III) from Hydrochloric Acid with Various Methoxy-substituted Triarylphosphines

Yuko Yamashoji, Takayuki Matsushita, Masanori Wada, Toshiyuki Shono

1988 Volume 17 Issue 1 Pages 43-46
Published: January 05, 1988
Released on J-STAGE: March 27, 2006

DOIhttps://doi.org/10.1246/cl.1988.43

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A series of methoxy substituted triarylphosphines R_nPh_3-np where R can be 2-MeOPh, 4-MeOPh, 2,6-MeOPh, and 2,4,6-MeOPh and n=1, 2, and 3, has been prepared and employed as extractants for gallium(III) from hydrochloric acid solutions. Their extractabilities for gallium(III) were found to become more effective with their increased basicities.

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Distinctive Photochemical Behavior of Rotationally Isomeric 2,5-(trans-4-Octeno)-p-benzoquinones

Masaru Miyake, Takashi Tsuji, Akio Furusaki, Shinya Nishida

1988 Volume 17 Issue 1 Pages 47-50
Published: January 05, 1988
Released on J-STAGE: March 27, 2006

DOIhttps://doi.org/10.1246/cl.1988.47

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Rotational isomers of 2,5-(trans-4-octeno)-p-benzoquinones, (1-A) and (1-B), behave distinctively in the photoreaction. The double bond in the side chain of 1-A cycloadds to the C (2) and C (5) of the quinone moiety, whereas 1-B is reluctant to do so. The results are interpreted in terms of frontier orbital interactions.

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Reactions of p-Benzoquinone Diimine Derivatives with N,N-Dimethylanilines

Yo Miyagi, Kazuhiro Maruyama, Mitsunori Kurokawa, Ayumi Yoshii

1988 Volume 17 Issue 1 Pages 51-54
Published: January 05, 1988
Released on J-STAGE: March 27, 2006

DOIhttps://doi.org/10.1246/cl.1988.51

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N,N′-Bisalkoxycarbonyl-p-benzoquinone diimine underwent a thermal addition reaction with N,N-dimethylanilines to form an N–C bond between an imino group and an N-methyl group. Upon irradiation the reaction was accerelated. The reaction did not proceed with N-alkyl substituted anilines other than methyl.

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A New Ambient Pressure Organic Superconductor Based on BEDT-TTF with T_C Higher than 10 K (T_C=10.4 K)

Hatsumi Urayama, Hideki Yamochi, Gunzi Saito, Kiyokazu Nozawa, Tadashi ...

1988 Volume 17 Issue 1 Pages 55-58
Published: January 05, 1988
Released on J-STAGE: March 27, 2006

DOIhttps://doi.org/10.1246/cl.1988.55

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An ambient pressure superconductivity of (BEDT-TTF)₂Cu(SCN)₂ was observed by d.c. magnetic susceptibility and electrical conductivity measurements. The superconducting critical temperature is the highest (T_C=10.4 K) among the organic superconductors so far obtained, even though the anion has a positional disorder in the crystal.

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Diastereofacial Control in the Reaction of Chiral α-Amino Ketones with Several Organometallics

Tamotsu Fujisawa, Makoto Funabora, Yutaka Ukaji, Toshio Sato

1988 Volume 17 Issue 1 Pages 59-62
Published: January 05, 1988
Released on J-STAGE: March 27, 2006

DOIhttps://doi.org/10.1246/cl.1988.59

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The addition reaction of organometallics to chiral α-amino ketones, prepared from α-halo ketones and (S)-2-methoxymethylpyrrolidine as a chiral auxiliary, gave different diastereomers of chiral amino alcohols depending on the difference of coordination ability of the metal used, i.e. organometallics such as Grignard reagent, organozinc, and cerium reagents preferred re-face attack, while organolithium compound attacked from si-face.

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Selective Displacement of a Triphenylphosphine Ligand in Triorgano(triphenylphosphine)gold(III) with Alkyl Lithiums Affording Tetraalkylaurates(III)

Sanshiro Komiya, Isao Endo, Satoshi Ozaki, Yasushi Ishizaki

1988 Volume 17 Issue 1 Pages 63-66
Published: January 05, 1988
Released on J-STAGE: March 27, 2006

DOIhttps://doi.org/10.1246/cl.1988.63

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Reactions of cis- and trans-dimethylethyl(triphenylphosphine)gold(III) with ethyl lithium selectively afford anionic square planar cis- and transdimethyldiethylaurates(III), respectively. On hydrolysis, the former gives cis-methyldiethyl(triphenylphosphine)gold(III), whereas the latter transdimethylethyl(triphenylphosphine)gold(III).

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ESR of Radical Anion and Radical Trianion of [1,2,5]Thiadiazolo-tetracyanonaphthoquinodimethane

Masatoshi Hirayama, Akihiko Seki, Yoshiro Yamashita, Takanori Suzuki, ...

1988 Volume 17 Issue 1 Pages 67-70
Published: January 05, 1988
Released on J-STAGE: March 27, 2006

DOIhttps://doi.org/10.1246/cl.1988.67

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The radical trianion of the title compound as well as its radical anion, formed by the electrolytic reduction in acetonitrile in the presence of nBu₄NClO₄ at room temperature, was characterized by the analysis of their ESR spectra.

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Photorearrangement of 4,4,5,5-Tetramethoxycyclohepta-2,6-dienones to 6,6,7,7-Tetramethoxybicyclo[3.2.0]hept-3-en-2-ones

Akira Mori, Tadahiko Kubota, Hitoshi Takeshita

1988 Volume 17 Issue 1 Pages 71-72
Published: January 05, 1988
Released on J-STAGE: March 27, 2006

DOIhttps://doi.org/10.1246/cl.1988.71

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The photorearrangement of 2,6-cycloheptadienones to bicyclo[3.2.0]hept-3-en-2-ones was observed. The bicycloketones further photoisomerized to bicyclo[2.2.1]heptenones via a [1,3] sigmatropy.

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Formation of [η⁵,η¹–C₅H₄C (OCOR)=C(OCOR)CO]Fe(CO)₂ Complexes via Triple CO Insertion into Cyclopentadienyl Anions by Fe(CO)₅

Saburo Nakanishi, Takehiro Hirano, Yoshio Otsuji

1988 Volume 17 Issue 1 Pages 73-76
Published: January 05, 1988
Released on J-STAGE: March 27, 2006

DOIhttps://doi.org/10.1246/cl.1988.73

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The reaction of cyclopentadienyl anions with Fe(CO)₅ in the presence of acyl chlorides gave [η⁵,η¹–C₅H₄C (OCOR)=C(OCOR) CO] Fe(CO)₂ complexes, accompaning a triple CO insertion into the anions and a double acylation.

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Synthesis of Optically Active myo-Inositol 1,3,4-Trisphosphate

Shoichiro Ozaki, Masayasu Kohno, Hiroyuki Nakahira, Motonobu Bunya, Yu ...

1988 Volume 17 Issue 1 Pages 77-80
Published: January 05, 1988
Released on J-STAGE: March 27, 2006

DOIhttps://doi.org/10.1246/cl.1988.77

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Synthesis of optically active myo-inositol 1,3,4-trisphosphate has been accomplished. Efficiency of a chiral HPLC column for optical resolution of myo-inositols is shown.

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Synthesis of a 3 (2H)-Furanone Derivative from Propargylic Alcohol, CO, and Phenyl Halide Catalyzed by Transition Metal Complexes

Yoshio Inoue, Masaaki Taniguchi, Harukichi Hashimoto, Kunihiro Ohuchi, ...

1988 Volume 17 Issue 1 Pages 81-82
Published: January 05, 1988
Released on J-STAGE: March 27, 2006

DOIhttps://doi.org/10.1246/cl.1988.81

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2-Methyl-3-butyn-2-ol reacted with CO and phenyl halides in the presence of a catalytic amount of transition metal complexes to afford 2,2-dimethyl-5-phenyl-3 (2H)-furanone (bullatenone) under the influence of CO₂.

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Enantioselective Synthesis of erythro-β-Hydroxy-L-histidine, the Pivotal Amino Acid of Bleomycin–Fe(II)–O₂ Complex

Takashi Owa, Masami Otsuka, Masaji Ohno

1988 Volume 17 Issue 1 Pages 83-86
Published: January 05, 1988
Released on J-STAGE: March 27, 2006

DOIhttps://doi.org/10.1246/cl.1988.83

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erythro-β-Hydroxy-L-histidine, a novel amino acid constituent of bleomycin, has been synthesized enantioselectively via the reaction of (N-pyruvylideneglycyl-D-phenylalaninato)copper(II) with imidazole-4-carbaldehyde.

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Synthesis of Aminoalcohols via Perihydro-1,3-oxazin-2-ones and Absolute Configuration Assignment through MM2 Calculations

Alessandro Bongini, Giuliana Cardillo, Mario Orena, Gianni Porzi, Serg ...

1988 Volume 17 Issue 1 Pages 87-90
Published: January 05, 1988
Released on J-STAGE: March 27, 2006

DOIhttps://doi.org/10.1246/cl.1988.87

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Diastereomeric perihydro-1,3-oxazin-2-ones are useful intermediates to enantiomerically pure aminoalcohols: their absolute configuration is assigned from ¹H NMR data and supported by MM2 calculations.

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The Stereoselective Michael Reaction of α,β-Unsaturated Thioesters with Silyl Enol Ethers Promoted by Combined Use of Antimony(V) Chloride and Tin(II) Triflate

Shu Kobayashi, Masanori Tamura, Teruaki Mukaiyama

1988 Volume 17 Issue 1 Pages 91-94
Published: January 05, 1988
Released on J-STAGE: March 27, 2006

DOIhttps://doi.org/10.1246/cl.1988.91

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α, β-Unsaturated thioesters react with silyl enol ethers to afford the corresponding Michael adducts stereoselectively in high yields by the use of a new catalyst, combined use of antimony(V) chloride and tin(II) triflate.

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Spectroscopic Evidence for the Inter-Chain Charge–Transfer Interaction in Copper-bis(2,5-dimethyl-N,N′-dicyanoquinonediimine), Cu(2,5-DM-DCNQI)₂

Kyuya Yakushi, Gen Ojima, Akito Ugawa, Haruo Kuroda

1988 Volume 17 Issue 1 Pages 95-98
Published: January 05, 1988
Released on J-STAGE: March 27, 2006

DOIhttps://doi.org/10.1246/cl.1988.95

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Polarized reflectance spectra of the single crystals of Cu(2,5-DM-DCNQI)₂ and Na(2,5-DM-DCNQI)₂ were measured at room temperature. The spectrum of Cu(2,5-DM-DCNQI)₂ clearly indicated the inter-chain interaction through the coordinate bonds, whereas the spectrum of Na(2,5-DM-DCNQI)₂ showed a typical one-dimensional feature along the stacking direction.

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Recognition–Adsorption of Artificial Liposomes onto Glass Surface Modified with Octadecylsilyl Monolayer

Kazuo Yamamura, Hitoshi Hatakeyama, Iwao Tabushi

1988 Volume 17 Issue 1 Pages 99-102
Published: January 05, 1988
Released on J-STAGE: March 27, 2006

DOIhttps://doi.org/10.1246/cl.1988.99

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Octadecylsilyl(ODS) modified glass support having R–NH₂ in the template cavity on ODS, (H₂N–R)_y·ODS[SiO₂], adsorbed negatively charged artificial liposomes, (X⁽ⁱ⁾/Lip·CL⁻), opening a way to a new unique supramolecular assembly system.

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Electron Transfer Reaction between Fe₄S₄ Cluster and Methyl Viologen

Nobumasa Kitajima, Sumio Noda, Shigetoshi Aono, Ichiro Okura, Yoshihik ...

1988 Volume 17 Issue 1 Pages 103-106
Published: January 05, 1988
Released on J-STAGE: March 27, 2006

DOIhttps://doi.org/10.1246/cl.1988.103

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The reduction of Fe₄S₄²⁺ to Fe₄S₄¹⁺ with the reduced form of methyl viologen, was found to proceed with the synthetic clusters ligated with pentafluorobenzenethiolate.

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Design of a New Host Compound, 2,2-Di(p-hydroxyphenyl)propane, and Crystal Structure of Its 1:1 Complex with Methylhydrazine

Fumio Toda, Koichi Tanaka, Tosiharu Hyoda, Thomas C. W. Mak

1988 Volume 17 Issue 1 Pages 107-110
Published: January 05, 1988
Released on J-STAGE: March 27, 2006

DOIhttps://doi.org/10.1246/cl.1988.107

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A new host compound, 2,2-di(p-hydroxyphenyl)propane, which exhibits high inclusion ability towards phenols, amines, and hydrazines, has been designed. The crystal structure of its 1:1 complex with methylhydrazine comprises centrosymmetric cyclic dimeric units consolidated by O–H···N hydrogen bonding.

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Total Synthesis of (+)-Goniothalenol [(+)-Altholactone], a Novel Bioactive Tetrahydrofurano-2-pyrone

Kin-ichi Tadano, Yoshihide Ueno, Seiichiro Ogawa

1988 Volume 17 Issue 1 Pages 111-114
Published: January 05, 1988
Released on J-STAGE: March 27, 2006

DOIhttps://doi.org/10.1246/cl.1988.111

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A novel plant-origin tetrahydrofurano-2-pyrone, (+)-goniothalenol has been synthesized from L-arabinose. The central feature of the present synthesis is a silica-gel catalyzed intramolecular epoxy ring opening by hydroxyl group for construction of the tetrahydrofuran in the title compound.

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Biosynthesis of Cyclic Monoterpenoids. Involvement of Stereochemically Specified Linalyl Cation in the Cyclization of C₁₀-Prenyl Chain

Takayuki Suga, Toshifumi Hirata, Shunsuke Izumi, Yoshikazu Hiraga, Kaz ...

1988 Volume 17 Issue 1 Pages 115-118
Published: January 05, 1988
Released on J-STAGE: March 27, 2006

DOIhttps://doi.org/10.1246/cl.1988.115

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Incubation of geranyl diphosphate (GPP) and the enantiomers and racemate of linalyl diphosphate (LPP) with the limonene synthetase isolated from Mentha spicata resulted in the conversion of GPP and (S)-LPP into (S)-limonene; this can be taken as evidence that linalyl cation having not only the (S)-LPP-like configuration but also C-1 and C-6 double bonds situated in the anti spatial arrangement is involved in the process of the cyclization of GPP to (S)-limonene. The intermediacy of the linalyl cation was supported by the evaluation of the potential energy of the cation with the MO calculation.

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p-Bis(diphenylhydrosilyl)benzene. A Useful Reagent for the Deoxygenation of Alcohols via Acetates

Hiroshi Sano, Toshimitsu Takeda, Toshihiko Migita

1988 Volume 17 Issue 1 Pages 119-122
Published: January 05, 1988
Released on J-STAGE: March 27, 2006

DOIhttps://doi.org/10.1246/cl.1988.119

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Acetates which were derived from primary, secondary, and tertiary alcohols were deoxygenated to the corresponding hydrocarbons in high yield by p-bis(diphenylhydrosilyl)benzene under homolytic conditions.

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Structures of Metasequoic Acid A and B

Fujio Sakan, Takashi Iwashita, Nobuyuki Hamanaka

1988 Volume 17 Issue 1 Pages 123-126
Published: January 05, 1988
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DOIhttps://doi.org/10.1246/cl.1988.123

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Two new antifungal diterpenes, metasequoic acid A(4) and B(5) were isolated from Metasequoia glyptostroboides Hu et Cheng. These compounds possess a new skeleton which contains a cyclopropane ring bridging C-3 and C-4 of the labdane framework. The structures 4 and 5 have been determined by spectroscopic methods.

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Perfluoroalkyl-thwarted Rearrangement of Quinol Esters. Formation of Catechol Derivatives via 1,3-Migration of Acyloxyl Group

Hitomi Suzuki, Yasukazu Shiraishi, Kazuhiro Shimokawa, Hidemitsu Uno

1988 Volume 17 Issue 1 Pages 127-130
Published: January 05, 1988
Released on J-STAGE: March 27, 2006

DOIhttps://doi.org/10.1246/cl.1988.127

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Treatment of 4-perfluoroalkyl-4-quinols with acetic anhydride-sulfuric acid was found to lead to 1,2- and 1,3-migration of acetoxyl group in initially formed quinol acetates followed by aromatization to give a mixture of 4-perfluoroalkylresorcinol diacetate and 4-perfluoroalkylcatechol diacetate.

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New Chiral Shift Reagents, Optically Active 2,2′-Dihydroxy-1,1′-binaphthyl and 1,6-Di(o-chlorophenyl)-1,6-diphenylhexa-2,4-diyne-1,6-diol

Fumio Toda, Koji Mori, Jyoji Okada, Manabu Node, Akichika Itoh, Kyoko ...

1988 Volume 17 Issue 1 Pages 131-134
Published: January 05, 1988
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DOIhttps://doi.org/10.1246/cl.1988.131

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The title compounds were found to be useful as a chiral shift reagent in ¹H NMR spectroscopy to determine enantiomeric purity of amines, alcohols, sulfoxides, selenoxides, phosphine oxides, phosphinates, and arsenoxides. It is also reported that the induced chemical shift difference increases when the title compound is used together with the typical chiral shift reagent, Eu(hfc)₃.

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Regio- and Stereoselective Trapping of Pentadienyl Anion by a Tin Electrophile

Yoshinori Naruta, Yutaka Nishigaichi, Kazuhiro Maruyama

1988 Volume 17 Issue 1 Pages 135-138
Published: January 05, 1988
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DOIhttps://doi.org/10.1246/cl.1988.135

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Electrophilic trapping of the pentadienyl anions bearing a methoxymethyl group with Me₃SnBr gives Z-pentadienylstannanes in high regioselectivity regardless of the structure of the anion.

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Solid-State NMR of H₃PW₁₂O₄₀·nH₂O and H₃PW₁₂O₄₀·6C₂H₅OH

Yuji Kanda, Kwan Young Lee, Shin-ichi Nakata, Sachio Asaoka, Makoto Mi ...

1988 Volume 17 Issue 1 Pages 139-142
Published: January 05, 1988
Released on J-STAGE: March 27, 2006

DOIhttps://doi.org/10.1246/cl.1988.139

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High-resolution solid-state ¹H and ³¹P NMR revealed that there were at least three different states for protons of H₃PW₁₂O₄₀·nH₂O; (i) protons present in highly hydrated samples, (ii) protonated water which is hydrogen-bonded to terminal oxygen, W = O···H⁺ (H₂O)₂ (n \doteqdot 6), and (iii) proton which is directly bonded to bridging oxygen, W–OH–W (n \doteqdot 0). When water was replaced by ethanol, a protonated ethanol species was detected by ¹H, ¹³C, and ³¹P NMR.

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A Short Synthesis of 15-Dehydroprostaglandin B₁ Methyl Ester

Hirokazu Naora, Takashi Ohnuki, Asao Nakamura

1988 Volume 17 Issue 1 Pages 143-144
Published: January 05, 1988
Released on J-STAGE: March 27, 2006

DOIhttps://doi.org/10.1246/cl.1988.143

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A new synthetic method for 15-dehydroprostaglandin B₁ methyl ester (15-dehydroPGB₁ methyl ester) in four steps from commercially available starting materials is described.

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Photoarylmethylation of 1,4-Dicyanonaphthalene by Use of Group 14 Organometallic Compounds

Kazuhiko Mizuno, Kiyotaro Terasaka, Masahiro Yasueda, Yoshio Otsuji

1988 Volume 17 Issue 1 Pages 145-148
Published: January 05, 1988
Released on J-STAGE: March 27, 2006

DOIhttps://doi.org/10.1246/cl.1988.145

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The photoreaction of 1,4-dicyanonaphthalene (DCN) with arylmethylsilanes, germane, and stannane in polar solvents gave the arylmethylated products of DCN in high yields. The fluorescence of DCN was efficiently quenched both in polar and nonpolar solvents by these group 14 organometallic compounds. In cyclohexane, the emission from the exciplex between DCN and arylmethylsilanes was observed. The mechanistic features of the photoreaction are described.

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A Novel One-Step Nickel-Mediated Synthesis of C₆Ar₆ Conjugated Hydrocarbons, Highly Substituted and Overcrowded Fulvenes and 3,4-Dimethylenecyclobutenes

Masahiko Iyoda, Akira Mizusuna, Masaji Oda

1988 Volume 17 Issue 1 Pages 149-152
Published: January 05, 1988
Released on J-STAGE: March 27, 2006

DOIhttps://doi.org/10.1246/cl.1988.149

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Nickel-catalyzed cyclo-oligomerization of aryl-substituted 1,1-dibromoethylenes in the presence or absence of diarylacety-lenes produces 1,2,3,4,6,6-hexaarylfulvenes and/or 1,2-diaryl-3,4-bis(diarylmethylene)cyclobutenes in moderate yields, providing a new and simple method for C₆Ar₆ conjugated hydrocarbons, highly overcrowded systems.

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A Soluble Poly(arylene) with Large Degree of Depolarization. Poly(2,5-pyridinediyl) Prepared by Dehalogenation Polycondensation of 2,5-Dibromopyridine with Ni(0)-Complexes

Takakazu Yamamoto, Takayori Ito, Kenji Kubota

1988 Volume 17 Issue 1 Pages 153-154
Published: January 05, 1988
Released on J-STAGE: March 27, 2006

DOIhttps://doi.org/10.1246/cl.1988.153

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Poly(2,5-pyridinediyl) was prepared by dehalogenation polycondensation of 2,5-dibromopyridine with Ni(0)-complexes. The polymer was soluble in formic acid, and the solution showed λ_max at about 370 nm and large degree of depolarization.

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Remarkable Effect of the Wavelength in the Photoassisted Carbonylation of the C–H Bond of Decane in the Presence of RhCl(CO)(PR₃)₂ as the Catalyst

Toshiyasu Sakakura, Koushi Sasaki, Yuko Tokunaga, Keisuke Wada, Masato ...

1988 Volume 17 Issue 1 Pages 155-158
Published: January 05, 1988
Released on J-STAGE: March 27, 2006

DOIhttps://doi.org/10.1246/cl.1988.155

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RhCl(CO)(PR₃)₂-catalyzed and photoassisted carbonylation of decane leading to the formation of C₁₁ aldehydes and/or 1-nonene was remarkably affected by the wavelength; irradiation with λ > 295 nm was essential to the formation of 1-nonene and undecanal. By cutting off λ > 325 nm, 1-nonene formation was completely suppressed, and a series of isomeric C₁₁ aldehydes were obtained.

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Photoinduced Preparation of Geometrical Isomers of [RuX(2mqn)₂(NO)] (X = Cl or Br; 2mqn = 2-Methyl-8-quinolinolate Ion) from Two Kinds of the Cis Isomers

Hiromi Kamata, Yoshiaki Konishi, Yoshimi Kamata (née Ogino), Ei ...

1988 Volume 17 Issue 1 Pages 159-162
Published: January 05, 1988
Released on J-STAGE: March 27, 2006

DOIhttps://doi.org/10.1246/cl.1988.159

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trans-[RuX(2mqn)₂(NO)] (X = Cl or Br; 2mqn = 2-methyl-8-quinolinolate ion) was prepared photochemically from two kinds of the cis isomers, cis (O,O),cis (N,N)- and cis (O,O),trans (N,N)-[RuX(2mqn)₂(NO)], in deoxygenated dichloromethane or dibromomethane. From the former cis isomer, the latter cis isomer was also prepared.

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Isolation and Structure of Magnoloside A, a New Phenylpropanoid Glycoside from Magnolia obovata Thunb.

Takashi Hasegawa, Yoshiyasu Fukuyama, Toshihide Yamada, Kazuyuki Nakag ...

1988 Volume 17 Issue 1 Pages 163-166
Published: January 05, 1988
Released on J-STAGE: March 27, 2006

DOIhttps://doi.org/10.1246/cl.1988.163

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Magnoloside A, a novel phenylpropanoid glycoside has been isolated from the MeOH extract of Magnolia obovata and its structure has been elucidated as 3,4-dihydroxy-β-phenyl-ethyl-O-α-L-rhamnopyranosyl-(1→2)-3-O-caffeoyl-β-D-allopyranoside by means of spectroscopic and chemical evidences.

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