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Akira Tahara, Masayuki Shimagaki, Rikagaku Kenkyusho, Masayoshi Itoh, ...
1974 Volume 3 Issue 7 Pages
651-654
Published: July 05, 1974
Released on J-STAGE: March 27, 2006
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Dehydroabietic acid (
1) was converted into
14 and
20 having the steroidal skeleton, by the use of its isopropyl group for the formation of the steroidal
D-ring.
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Josuke Tsunetsugu, Masaru Sato, Seiji Ebine
1974 Volume 3 Issue 7 Pages
655-658
Published: July 05, 1974
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Tropenylation of 3,4,5-trimethoxyaniline (
II) with tropenylium ion (
I), generated by action of acid on 7-ethoxy-1,3,5-cycloheptatriene, gave
C-tropenyl derivative (
III) and its Schiff base (
VI). Further reaction of (
III) with (
I) gave not only tropenylation products (
IV) and (
XI) but also detropenylation product (
II). Detropenylation has proved to take place in the presence of acid.
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Katsuyuki Ogura, Shigeko Furukawa, Gen-ichi Tsughihashi
1974 Volume 3 Issue 7 Pages
659-662
Published: July 05, 1974
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The carbanion (
2) generated from methyl methylthiomethyl sulfoxide (
1) reacts with an ester to afford an acylated product (
3). This compound can be transformed into derivatives of the corresponding α-hydroxyaldehyde and also into the ester which has one more methylene group than the original ester (Scheme 2).
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Masashi Araki, Teruaki Mukaiyama
1974 Volume 3 Issue 7 Pages
663-666
Published: July 05, 1974
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It was found that common ketones were prepared in good yields by the reaction of grignard reagents with mixed carboxylic anhydrides composed of o-substituted benzoic acids or pivalic acid and common carboxylic acids at −20 or −78°C. Further, it was established that a 1,4-diketone such as 2,5-dioxoundecane, a precursor of dihydrojasmone was synthesized in 71∼82% yields from levulinic acid by one step procedure without protecting its carbonyl group.
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Akira Nishinaga, Toshio Itahara, Teruo Matsuura
1974 Volume 3 Issue 7 Pages
667-670
Published: July 05, 1974
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Oxygenation of 2,6-di-
t-butyl-4-alkylphenols catalyzed by Bu
tOK in aprotic solvents has been found newly to form 4-hydroxy-5,6-epoxy-2-cyclohexenones (
2) in excellent yield. A mechanism by which
2 is formed envisaging intramolecular participation of the π-system in the degradation of 4-oxo-2,5-cyclohexadienyl peroxide ion (
11) primarily formed as transient intermediate is discussed. 2,4-Di-
t-butylphenols also gave epoxy-
p-quinols in the same system.
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Shigeru Oae, Tadamitsu Sakurai, Hirokazu Kimura, Seizi Kozuka
1974 Volume 3 Issue 7 Pages
671-674
Published: July 05, 1974
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O-Benzoyl-
N-(
p-toluenesulfonyl)arylhydroxylamines (
I) were found to rearrange thermally giving
o-acyloxy-
p-toluenesulfonanilides (
II) in quantitative yields. An intramolecular concerted cyclic process has been suggested for the rearrangement on the basis of
18O tracer study. The solvent and the substituent effects on the mechanism of this novel 1,3-acyloxy migration were also examined.
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Akiyoshi Matsuzaki, Saburo Nagakura
1974 Volume 3 Issue 7 Pages
675-678
Published: July 05, 1974
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Fluorescence from the
1A
2 state of CS
2 was found to be quenched by a magnetic field. This is the first observation of the magnetic quenching of emission from the excited singlet state. The quenching was found to be due to the enhancement of intramolecular nonradiative energy transfer by a magnetic field.
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Masaki Otagiri, Ken Ikeda, Kaneto Uekama, Osamu Ito, Masahiro Hatano
1974 Volume 3 Issue 7 Pages
679-682
Published: July 05, 1974
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When cyclohexanone and its methyl derivatives were included in the cavities of cyclodextrins, the induced circular dichroism (CD) bands were observed in the absorption region of n-π
* transition of the carbonyl chromophore. The sign of induced CD band of 2-methylcyclohexanone included in β-cyclodextrin was same as that of resolved
R-isomer. From these observations the mode of inclusion and structure of β-cyclodextrin complex with methylcyclohexanone were discussed.
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Giuseppe Condorelli, Ignazio Fragala, Salvatore Giuffrida
1974 Volume 3 Issue 7 Pages
683-686
Published: July 05, 1974
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N,
N′-1,3-propylene-bis(salicylideneiminato)Cu(II) reacts with some uranyl salts to form bi- and trinuclear complexes. Infrared data show that the “complex ligand” is coordinated to the uranyl ion in the equatorial plane through the phenolic oxygens. Diffuse reflectance spectra suggest a copper(II) environment more distorted from planarity in polynuclear species than the “complex ligand”.
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Masashi Araki, Shigeru Sakata, Hisashi Takei, Teruaki Mukaiyama
1974 Volume 3 Issue 7 Pages
687-688
Published: July 05, 1974
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It was found that mixed carboxylic anhydrides of γ- or ε-oxocarboxylic acids react with Grignard reagents to give 1,4- or 1,6-diketones in 32∼71% yields by one step procedure.
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Eiichiro Shimada, Katsuhiko Inomata, Teruaki Mukaiyama
1974 Volume 3 Issue 7 Pages
689-690
Published: July 05, 1974
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It was suggested that vinyloxytin was produced by passing gaseous ketene into a methylene chloride solution of tin alkoxide at low temperature. The vinyloxytin thus formed further reacted with various carbonyl compounds at low temperature in the presence of strong Lewis acid such as TiCl
4, or AlCl
3 to give the corresponding β-hydroxyalkanoates.
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Junji Kimura, Yoshiyuki Fujisawa, Takamichi Sawada, Oyo Mitsunobu
1974 Volume 3 Issue 7 Pages
691-692
Published: July 05, 1974
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The reaction of uridine, triphenylphosphine (I) and diethyl azodicarboxylate (II) in THF gave 2′,3′-
O-(triphenyl)phosphoranyl-
O2,5′-cyclouridine (III). The alkaline or acid hydrolysis of III gave uridine and triphenylphosphine oxide (1:1). The treatment of III in THF-water afforded
O2,5′-cyclouridine. The reaction of III with methanol under reflux gave
O2-methyluridine.
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Fujito Nemoto, Fumio Shimoda, Kazuhiko Ishizu
1974 Volume 3 Issue 7 Pages
693-697
Published: July 05, 1974
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Utilizing ENDOR observations for the 4,4′-diisopropylbiphenyl anion, the β-proton coupling constants were determined and their temperature dependence was investigated. The positive temperature dependence of the β-proton coupling constant was interpreted utilizing a revised model of restricted rotation for isopropyl groups (see Fig.3-b). The energy difference, E
o between the two equilibrium states of this restricted rotational system was estimated to be 0.4 Kcal/mol.
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Kunio Nikki, Naoya Nakagawa
1974 Volume 3 Issue 7 Pages
699-700
Published: July 05, 1974
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NMR solvent shifts induced by C
6F
6 have been interpreted as resulting from a dipole-quadrupole interaction.
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Kiyosi Kondo, Masakatsu Matsumoto
1974 Volume 3 Issue 7 Pages
701-704
Published: July 05, 1974
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Base-catalyzed isomerization of 3,6-dihydro-1,2-dioxins followed by dehydration and the isomerization in the presence of primary amines provide useful, high yield routes to furans and pyrroles, respectively.
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Susumu Kobayashi, Teruaki Mukaiyama
1974 Volume 3 Issue 7 Pages
705-708
Published: July 05, 1974
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The new method for the stereospecific synthesis of trisubstituted olefin was successfully applied to a highly stereoselective synthesis of 1,5-diene unit, demonstrating the preparation of ethyl geranate [3] starting from 3-methyl-2-butenyl bromide [1].
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Yoshiaki Ohgo, Yukikazu Natori, Seiji Takeuchi, Juji Yoshimura
1974 Volume 3 Issue 7 Pages
709-712
Published: July 05, 1974
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Bis(dimethylglyoximato)cobalt(II)-quinine-catalyzed asymmetric hydrogenation of α-diketones afforded optically active reduction products, while that of α-oxocarboxylates and diacetyl gave not only simple reduction products but also
reductive dimerization products with optical activity. In general, the optical yields of simple reduction products in cases of α-diketones (56–73%) were higher than those in cases of α-oxocarboxylates (12–20%).
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Teruo Matsuura, Yoshihiro Shigemasa, Chikahiro Sakazawa
1974 Volume 3 Issue 7 Pages
713-714
Published: July 05, 1974
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The course of the calcium hydroxide-catalyzed reaction of formalin to give monosaccharides was potentiometrically followed. Changes of the oxidation-reduction potential curve obtained were found to correspond satisfactorily to the reaction phases; induction period, accumulation of C
3 products, saccharide formation, and gradual decomposition of saccharides, successively.
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Takayuki Suga, Toshifumi Hirata, Kazuo Tori
1974 Volume 3 Issue 7 Pages
715-718
Published: July 05, 1974
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The structure of aloenin, a bitter glucoside from
Aloe species, has been reinvestigated and elucidated to be 6-(2′-β-
D-glucopyranosyloxy-4′-hydroxy-6′-methyl)phenyl-4-methoxy-2-pyrone (
2) by a combination of the chemical and spectroscopic methods.
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Kazuhiro Maruyama, Seiiti Arakawa
1974 Volume 3 Issue 7 Pages
719-720
Published: July 05, 1974
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2-Acyl-3-methyl-1,4-naphthoquinone-2,3-epoxide(
1) isomerizes photochemically to give lactone. The spectral data and chemical reactions of the lactone are compatible with structure(
2). Photochemical reaction of (
1) with xanthene was also described.
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Kazuhiro Maruyama, Toshifumi Miyazawa, Yasuo Kishi
1974 Volume 3 Issue 7 Pages
721-724
Published: July 05, 1974
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Photochemical reactions between
o-chloranil and aldehydes were extensively studied. In the reactions with iso-butyraldehyde and 2-ethylbutyraldehyde, photo-adducts of a novel type proved to be produced. The structure of these photo-adducts determined by IR, PMR, and mass spectra, and by elemental analysis was compatible with 3,3-dialkyl-5,6,7,8-tetrachloro-2,3-dihydro-1,4-benzodioxin-2-ol (II).
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Masatoshi Hirayama, Michihiko Sato
1974 Volume 3 Issue 7 Pages
725-728
Published: July 05, 1974
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An attempt was made for the separation of contact term contributions from the Pr(FOD)
3- and Eu(FOD)
3-induced
1H and
13C shifts in aniline and
p-toluidine, by using the contact shift pattern estimated theoretically. This suggested the transfer of negative and positive spin from the Eu ion and the Pr ion, respectively.
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Takeo Taguchi, Yoshinari Sato, Kenzo Watanabe, Teruaki Mukaiyama
1974 Volume 3 Issue 7 Pages
729-730
Published: July 05, 1974
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4-(4-Carboxybutyl)-1,2-dihydrothieno[3,4-
d]imidazol-2-one [I], a precusor of dl-biotin, was synthesized via 6 steps starting from 4-methyl-2(1
H)-imidazolone.
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Takeshi Nakai, Makoto Okawara
1974 Volume 3 Issue 7 Pages
731-732
Published: July 05, 1974
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Treatment of the title compound with
n-butyllithium produces the lithiomethylene derivative (
4) . The reagent
4 so generated has been shown to serve effectively as an equivalent of the formyl anion by alkylation of
4 with alkyl halides followed by hydrolysis with mercuric ion to the corresponding aldehyde.
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Hiroaki Nakayama, Chiho Nishijima, Satoshi Tachiyashiki
1974 Volume 3 Issue 7 Pages
733-736
Published: July 05, 1974
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Gas phase reactions of thallium(I) cation with several ligands were investigated by the use of hexafluoroacetylacetonatothallium(I) as a precursor of the ion. 1:1 complex formation with thallium(I) was observed.
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Ryoko Matsuzaki, Atsuko Sofue, Hagio Masumizu, Yuzo Saeki
1974 Volume 3 Issue 7 Pages
737-740
Published: July 05, 1974
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Bi
2(SO
4)
3 begins to decompose at 465°C, and the decomposition process of Bi
2(SO
4)
3 can be represented as follows: Bi
2(SO
4)
3\xrightarrow465°CBi
2O
3·2Bi
2(SO
4)
3\xrightarrow550°C2Bi
2O
3·Bi
2(SO
4)
3\xrightarrow580°C7Bi
2O
3·2Bi
2(SO
4)
3\xrightarrow830°C12Bi
2O
3·Bi
2(SO
4)
3\xrightarrow880°C28Bi
2O
3·Bi
2(SO
4)
3\xrightarrow920°CBi
2O
3.
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Kiyosi Kondo, Fumio Mori
1974 Volume 3 Issue 7 Pages
741-742
Published: July 05, 1974
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Various γ-lactones bearing vinylic substituent on β-position were obtained directly by the thermal condensation of
trans-2-alkene-1,4-diols with orthocarboxylic esters in the presence of a catalytic amount of hydroquinone or phenol.
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Ichiro Murata, Kazuhiro Nakasuji, Takamitsu Morita
1974 Volume 3 Issue 7 Pages
743-746
Published: July 05, 1974
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9-Methylenetricyclo[4.3.1.0]deca-2,4,7-triene (
3a) and its derivatives possessing electron releasing group such as bis(dimethylamino)- and bis(methylthio)-groups at the exo-methylene carbon atom (
3b and
3c) were synthesized from bicyclo[4.3.1]decatetraenyl anion (
2). It has been shown that the closed norcaradiene tautomers (
3a,
3b and
3c) are preferable to the opened nonafulvene tautomers (
4a,
4b, and
4c).
View full abstract
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Noboru Morita, Toyonobu Asao, Yoshio Kitahara
1974 Volume 3 Issue 7 Pages
747-750
Published: July 05, 1974
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Thermal isomerization of (2+8)cycloadducts of tropones and 8-oxoheptafulvene afforded 3-(cyclohexa-2,4-dienyl)-1-oxaazulan-2-ones by antarafacial [1,7] sigmatropic rearrangement which is a first example in a rigid system. An activation energy (21.4 kcal. mol
−1) and an entropy of activation (−25.8 e.u.) were obtained for the reaction.
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Noriyoshi Masuoka, Tadao Kamikawa, Takashi Kubota
1974 Volume 3 Issue 7 Pages
751-754
Published: July 05, 1974
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The synthesis of the title compound
20 modelled on the proposed biogenetic scheme is described. The key intermediate
11 has been synthesised by photocycloaddition followed by acid cleavage.
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Shizuo Fujiwara, Tokuko Watanabe, Takeko Inoue
1974 Volume 3 Issue 7 Pages
755-758
Published: July 05, 1974
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ESR study of Ir hot ions produced in γ-irradiated Ir(III) complexes has been carried out. It has been found that Ir(II) hot ions take d
7 configuration of low spin state. The unpaired electron is localized in d
3z2−r2 orbital in the elongated octahedral structure. Ir(IV) hot ions are found to be formed in irradiated Ir(III) hexachloro complexes.
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Masaaki Iwata, Sakae Emoto
1974 Volume 3 Issue 7 Pages
759-760
Published: July 05, 1974
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L’oxydation directe par oxygène moleéculaire des anthranols-2 aux anthraquinones-1,2 est étudiée. La réaction est spécifiquement catalysée par l’ion cuivrique. L’addition d’une molécule d’imidazole par atome de cuivre augmente énormemént la Vitesse initiale de la réaction.
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Hirokatsu Akagi, Eigo Takabatake, Yuzaburo Fujita
1974 Volume 3 Issue 7 Pages
761-764
Published: July 05, 1974
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The photosensitized methylation of inorganic mercury in the presence of solid sulfur was investigated in an aqueous acetic acid solution of mercuric acetate. It was found that the photooxidation of sulfur into sulfate ions coupled with the reduction of mercuric ions and the resulting sulfate ions reacted with mercuric acetate to produce basic mercuric sulfate, a yellow precipitate, which acted as an effective photosensitizer for the methylation.
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Jun Niwa, Mitsuru Yamazaki
1974 Volume 3 Issue 7 Pages
765-768
Published: July 05, 1974
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The
13C chemical shifts of carboxyl carbons of substituted benzoic acids in dimethyl sulfoxide-d
6 show a linear relationship with pK
a-values for
m- and electron-withdrawing
p-substituents, whereas for electron-donating
p-substituents they show upfield deviations from the regression line. The chemical shifts are determined by Yukawa–Tsuno’s equation with a negative r-value.
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Meiseki Katayama, Sadao Ushimaru
1974 Volume 3 Issue 7 Pages
769-772
Published: July 05, 1974
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The radiation-induced ionic polymerization of α-methylstyrene has been studied by means of the Hittorf type conductivity measurement. For extremely dry samples it has been estimated that the chain transfer to monomer is about 10
5. It was concluded that freely moving electrons play an important role in the polymerization.
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Shigeyasu Kuroda, Masaji Oda, Yoshio Kitahara
1974 Volume 3 Issue 7 Pages
773-776
Published: July 05, 1974
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Treatment of [2-(2,3,4,5-tetrachloro-1,3-cyclopentadienyl)vinyl]tropylium fluoroborate
9 with bases gave 8-(1,2,3,4-tetrachlorofulven-6-yl)heptafulvene
4. In similar way 8-(9-fluorenylidene)methyl heptafulvene
5 was also prepared.
4 is more polar than
5 is, but is less stable. Both
4 and
5 easily gave [8+2] cycloadducts with tetracyanoethylene.
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Minoru Hirota, Kazuo Todokoro
1974 Volume 3 Issue 7 Pages
777-780
Published: July 05, 1974
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The free energies of activation for the restricted rotation around the amide C–N bond has been determined for a series of o-substituted benzamides, and the extraordinarily low barrier in
o-hydroxybenzamide is attributed to the effect of the intramolecular hydrogen bond.
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Yoshinori Kidani, Shinobu Naga, Hisashi Koike
1974 Volume 3 Issue 7 Pages
781-784
Published: July 05, 1974
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Two kinds of Co(III) mixed ligand chelates with acetylacetone and oxine were newly synthesized, and their mass spectra were analyzed. A binding ratio of Co, acac, and oxine has been determined to be 1:2:1 and 1:1:2 respectively, and it was found that Co(acac)(oxine)
2 was more stable than Co(acac)
2(oxine) under electron impact.
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Isao Ikemoto, Kuniko Samizo, Takashi Fujikawa, Kikujiro Ishii, Toshiak ...
1974 Volume 3 Issue 7 Pages
785-790
Published: July 05, 1974
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The photoelectron spectra of TCNE and TCNQ in the gaseous state were measured by stimulating with He I resonance line. The first ionization potential is determined to be 11.77 eV for TCNE and 9.61 eV for TCNQ. The interpretations of the observed photoelectron spectra are carried out with the aids of the photoelectron spectroscopic data of the related compounds and the results of CNDO/2 calculation.
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Hiroshi Kimoto, Hiroshige Muramatsu, Kan Inukai
1974 Volume 3 Issue 7 Pages
791-794
Published: July 05, 1974
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Four 1-trifluoromethyl-1,2,2-trifluoroindanes(
IV) were synthesized in one step from alkylbenzenes(
I) and hexafluoropropene(
II) in the presence of di-
t-butyl peroxide. The dehydrofluorination of IV gave the corresponding 1-trifluoromethyl-1,2-difluoroindenes(
V).
View full abstract
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Otohiko Tsuge, Masashi Tashiro, Yoko (née Nishihara) Kiryu
1974 Volume 3 Issue 7 Pages
795-796
Published: July 05, 1974
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Enamines derived from cyclohexanone, propionaldehyde, and
n-butyraidehyde and secondary amines react with pyrrole and pyrazole, affording new Michael type adducts respectively.
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Mutsukazu Kamo, Hisao Kanda, Yoichiro Sato, Nobuo Setaka
1974 Volume 3 Issue 7 Pages
797-800
Published: July 05, 1974
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The cluster-like hydrocarbons characteristic of the pitch prepared from polyvinyl chloride at 400°C were not observed in the pitch prepared at 415°C. A reaction process in the early stage carbonization of the compound is proposed.
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Kazuhito Iuchi, Shintaro Asada, Akira Sugimori
1974 Volume 3 Issue 7 Pages
801-802
Published: July 05, 1974
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Dimethyl fumarate and fumaronitrile undergo photochemical ligand substitution toward hexakis(phenyl isocyanide)chromium(O). The coodinated dimethyl fumarate is eliminated in the dark without accompanying trans–cis isomerization. Dimethyl maleate, the
cis-isomer, does not undergo this type of photoreaction.
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Masuo Funabashi, Haruo Sato, Juji Yoshimura
1974 Volume 3 Issue 7 Pages
803-804
Published: July 05, 1974
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The title compounds were stereoselectively prepared from 3-
C-methylene-α-
D-ribo- and 5-
C-methylene-α-
D-xylo-hexofuranose derivatives by successive epoxidation and reduction, and from corresponding 3- and 5-uloses by the Grignard reaction, respectively.
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Yusaku Ikegami, Toyonobu Asao
1974 Volume 3 Issue 7 Pages
805-808
Published: July 05, 1974
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The ESR study of the 5-nitrosotropolonate anion radical generated electrolytically in
N,
N-dimethylformamide elucidated the restricted rotation around the C–N bond. The free energy of activation
ΔG
≠ for the rotation of 5-nitrosotropolone was estimated by the NMR study to be 16.5 kcal·mol
−1 in dimethylsulfoxide.
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Yoshio Nakamura, Hidefumi Hirai
1974 Volume 3 Issue 7 Pages
809-814
Published: July 05, 1974
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The complex of cross-linked polyacrylic acid with rhodium(111) catalyzes the heterogeneous hydrogenation of terminal and internal alkenes in polar solvents at 30°C under an atmospheric hydrogen pressure. The C=C double bonds can be hydrogenated selectively by the complex catalyst for the hydrogenation of the alkenes with carbonyl and aromatic groups.
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Sadao Arai, Takamichi Yamagishi, Mitsuhiko Hida
1974 Volume 3 Issue 7 Pages
815-816
Published: July 05, 1974
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New phosphonium salts were obtained by the reaction of 1-amino-2,4-dibromoanthraquinone or sodium 1-amino-4-bromoanthraquinone-2-sulfonate with tri-
n-butylphosphine in the presence of cuprous chloride. In these reactions, the bromine atom of anthraquinone derivatives was substituted by the phosphine to give phosphonium salts containing carbon–phosphorus bond.
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Takafumi Kanazawa, Takao Umegaki, Eiji Wasai
1974 Volume 3 Issue 7 Pages
817-818
Published: July 05, 1974
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Mg
3(PO
4)
2·8H
2O was prepared by converting Mg
3(PO
4)
2·22H
2O in an alkaline solution at a pH of about 9. The conversion period was reduced to 2–4 weeks by the addition of MgHPO
4·3H
2O to the 22-hydrate and the pH adjustment with Na
2CO
3.
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Daisuke Uemura, Yoshimasa Hirata
1974 Volume 3 Issue 7 Pages
819-822
Published: July 05, 1974
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Further investigation of constituents in title plants gave three new diterpenoids, named jolkinolides C, D, and E. In this report structural elucidation of those compounds was described.
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Nobuaki Tsuchihashi, Hiroyuki Nomori, Masahiro Hatano, Shigeo Mori
1974 Volume 3 Issue 7 Pages
823-826
Published: July 05, 1974
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Induced circular dichroism was found for achiral molecules when buried in the solid film of PMDG made by casting from solution. This circular dichroism is regarded to be induced by the dissymmetric field due to the supramolecular helical structure of PMDG molecules retained in the solid film.
View full abstract
