scispace - formally typeset
Search or ask a question

Showing papers on "Benzaldehyde published in 1968"


Journal ArticleDOI
TL;DR: The enzymes of the mandelate-to-benzoate pathway are non-specifically active on, and induced by, all the substituted analogues that support growth, and the possible regulation of the enzyme systems is discussed.
Abstract: 1. Bacterium N.C.I.B. 8250 was grown on dl-mandelate, benzyl alcohol, benzoyl-formate, benzaldehyde and benzoate and also on 2-hydroxy, 4-hydroxy, 3,4-dihydroxy and 4-hydroxy-3-methoxy analogues of these compounds. The enzymic complements of the cells were determined and the specificities of some of the enzymes examined. 2. Growth on mandelate or benzoylformate induces l-mandelate dehydrogenase, benzoylformate decarboxylase, benzyl alcohol dehydrogenase and a heat-stable as well as a heat-labile benzaldehyde dehydrogenase. Growth on benzyl alcohol or benzaldehyde induces benzyl alcohol dehydrogenase and the heat-labile benzaldehyde dehydrogenase. 3. The enzymes of the mandelate-to-benzoate pathway are non-specifically active on, and induced by, all the substituted analogues that support growth. 4. Benzoate oxidase is induced by growth on benzoate or on 2-hydroxybenzoate. 2-Hydroxybenzoate hydroxylase, 4-hydroxybenzoate hydroxylase and 4-hydroxy-3-methoxybenzoate O-demethylase are induced only by growth on homologous substrates. 5. The results of the investigation are discussed with regard to the possible regulation of the enzyme systems.

104 citations


Journal ArticleDOI
TL;DR: The reaction between olefins, N-chloroacetamide or 1,3-dibromo-5,5-dimethylhydantoin, and hydrogen peroxide affords β-halohydroperoxides in good yields as discussed by the authors.
Abstract: The reaction between olefins, N-chloroacetamide or 1,3-dibromo-5,5-dimethylhydantoin, and hydrogen peroxide affords β-halohydroperoxides in good yields These compounds react extremely rapidly in basic solution to give products which depend upon their structure The 3-halo-2,3-dimethyl-2-butyl hydroperoxides form 2,3-dimethyl-3-hydroperoxy-1-butene and from the 2-halo-1,2-dimethylcyclohexyl hydroperoxides 1-methyl-2-methylene-cyclohexyl hydroperoxide is obtained No allylic hydroperoxide can be detected from the reaction between base and 3-bromo-2-methyl-2-butyl hydroperoxide Mainly cleavage products, acetone and acetaldehyde, are formed together with some 2,3-epoxy-2-methylbutane The reaction between base and 2-bromo-1-phenylethyl hydroperoxide gives styrene oxide, benzoic acid, and some benzaldehyde From trans-2-bromocyclohexyl hydroperoxide, trans-2-bromocyclohexanol, cyclohexene oxide, and some trans-1,2-cyclohexanediol are obtained upon reaction with base No evidence for the formation of the ally

54 citations


Journal ArticleDOI
TL;DR: The pathways of oxidation of mandelate and related compounds were investigated by the technique of simultaneous adaptation and 3,4-dihydroxybenzoate underwent ring cleavage with the ultimate formation of β-oxoadipate.
Abstract: SUMMARY: Bacterium ncib 8250 was grown on mandelate, benzyl alcohol, benzoylformate, benzaldehyde or benzoate and also on 2-hydroxy, 4-hydroxy, 3,4-dihydroxy and 4-hydroxy-3-methoxy derivatives of these compounds. Growth rates and yields of organism were measured for many of the substrates. The pathways of oxidation of mandelate and related compounds were investigated by the technique of simultaneous adaptation. Bacterium ncib 8250 did not utilise D-mandelate; L-mandelate was oxidised via benzoylformate, benzaldehyde and benzoate to catechol. Benzyl alcohol was converted to catechol via benzaldehyde and benzoate. The 2-hydroxy-substituted compounds were oxidised to catechol by a parallel pathway. 4-Hydroxy-, 3,4-dihydroxy- and 4-hydroxy-3-methoxy-substituted compounds were all converted to 3,4-dihydroxybenzoate. Catechol and 3,4-dihydroxybenzoate underwent ring cleavage with the ultimate formation of β-oxoadipate.

39 citations


Journal ArticleDOI
TL;DR: In this article, a novel trans-anethole has been obtained photochemically, and the structure of the dimer has been ascertained as 1,cis-2-di-p-anisyl-trans-3,trans-4-dimethylcyclobutane.

38 citations


Journal ArticleDOI
TL;DR: The structure of the di-O-benzylidene derivatives obey the rules of Hann and Hudson as mentioned in this paper, and the corresponding amides and hydrazides on treatment with ammonium D -xylonate with benzaldehyde and hydrochloric acid gives the di O-bensylidenes-D -xylonic acid, whereas the D -ribonate and D -lyxonate salts give the 3,5-Obensyde-pentonolactones.

30 citations


Journal ArticleDOI
TL;DR: In this paper, the reaction of manganic acetate in glacial acetic acid with benzene (100 °C), chlorobenzene, or toluene (110 °C) indicate that HOOCCH2· radicals are the primary intermediates.

28 citations



Journal ArticleDOI
TL;DR: The benzophenone-sensitized photolysis of benzaldehyde anil in anhydrous alcoholic solvents in an atmosphere of oxygen has been shown to lead to the formation of 1,2,N,N-tetraphenylethylenediamine and 2-phenylquinoline as mentioned in this paper.

21 citations



Journal ArticleDOI
TL;DR: In this article, the photochemical behavior of 1,2,3-triphenylaziridine has been investigated and it has been shown that photolysis in cyclohexene affords a 1,3 cycloaddition product, 1, 2,3 -triphensyl octahydroisoindole as a mixture of two stereoisomers.

18 citations


Journal ArticleDOI
TL;DR: In this paper, the cobaltous acetate-catalyzed autoxidation of benzaldehyde in acetic acid has been investigated and the nature and the mechanism of the oxidation at high cobalt concentration (1·2−5 × 10−3 M) has been studied in detail.
Abstract: The cobaltous acetate-catalyzed autoxidation of benzaldehyde in acetic acid has been investigated and the nature and the mechanism of the oxidation at high cobaltous concentration (1·2–5 × 10–3 M) has been studied in detail. The induction period appearing at the beginning of the limiting rate region is explained by the inhibition brought about by the cobaltous ions. The inhibiting effect of the transition metal ions studied has been shown to be due to their electronic structure. The limiting rate of oxidation at high cobalt concentrations could be explained on the basis of the steady-state concentration of perbenzoic acid produced by the catalyst.


Journal ArticleDOI
TL;DR: In this article, the effects of an excess of zinc on the formation of styrene were investigated. But benzaldehyde was recovered almost unchanged in the reaction with zinc-methylene iodide complex in the absence of zinc.

Journal ArticleDOI
TL;DR: In this article, the penicillin nucleus at C-6 with benzaldehyde and formaldehyde was hydroxyalkylated with 6-AMino-6-(α-hydroxybenzyl)-penicillanic acid (6-APA) as starting material.
Abstract: The hydroxyalkylation of the penicillin nucleus at C-6 with benzaldehyde and formaldehyde is reported. 6-aminopenicillanic acid (6-APA) (2) was used as starting material. Protection of the functional groups and activation of the C-6 position were effected by converting 6-APA successively into the Schiff base 13, the methyl ester 14 and the copper complex 15. The latter gave with benzaldehyde the C-6 monosubstituted complex 17, and with formaldehyde the disubstituted complex 18. The direct α-hydroxybenzylation of 6-APA at C-6 was also carried out with an excess of benzaldehyde at pH 7,5 leading to the SCHIFF base 19. Mild hydrolysis of 19 gave 6-amino-6-(α-hydroxybenzyl)-penicillanic acid (21). Phenylacetylation of the latter yielded the penicillin G analogue 22. Direct reaction of 6-APA with formaldehyde took place only in the presence of salicylaldehyde, giving the oxazolidine 24, from which the amino acid 25 could not be obtained. The new compounds showed only weak antibacterial activity as compared with penicillin G.

Journal ArticleDOI
TL;DR: The catalytic activity of copper-iron-polyphthalocyanine was solvent-dependent: tetrahydrofuran, ethanol, acetonitrile, ethyl acetate and anisole inhibited the oxidation of benzaldehyde and saturated aliphatic aldehydes in benzene to afford corresponding peroxy acids and acids in quantitative yields.
Abstract: Copper-iron-polyphthalocyanine showed a specific catalysis for the oxidations of the substituted benzaldehydes and the saturated aldehydes with oxygen. The catalytic activity of copper-iron-polyphthalocyanine was solvent-dependent: tetrahydrofuran, ethanol, acetonitrile, ethyl acetate and anisole inhibited the oxidation of benzaldehyde by copper-iron-polyphthalocyanine and oxygen, while benzene and acetone resulted in catalytic oxidation. Benzaldehyde and the saturated aliphatic aldehydes in benzene were oxidized catalytically with copper-iron-polyphthalocyanine and oxygen to afford the corresponding peroxy acids and acids in quantitative yields. Furthermore, oxygen was absorbed with no induction period; the rate of oxygen absorption was in the range of 8–13 ml/min. On the other hand, the unsaturated aliphatic aldehydes, cinnamaldehyde and acrolein, were oxidized with a very slow rate of oxygen absorption in spite of the existence of copper-iron-polyphthalocyanine in the reaction system. p-Methylbenzaldeh...

Journal ArticleDOI
TL;DR: In this paper, the 4-benzyl-isoquinoline derivatives are briefly reviewed and the condensation of isoquinolinium salts with benzaldehyde under alkaline conditions has been examined; the structure originally proposed by Krohne 11 for one of these products has been corrected.

Journal ArticleDOI
01 Aug 1968-Talanta
TL;DR: The red colour that develops when mineral acids are added to solutions of dithizone (I; 3-mercapto-1,5-diphenylformazan) in certain samples of dioxan is mainly due to the formation of 2-methyl-3- phenyl-5-phenylazo-1-3,4-thiadiazoline (II) derived in part from adventitious traces of 2 -methyldioxalane.

Journal ArticleDOI
TL;DR: In this paper, a study of the reaction of benzhydrazide under various conditions has provided evidence that reaction occurs by way of the aroyldi-imide, and this can be diverted in Part to give benzaldehyde and thence, by further reactions, 2,5-diphenyloxadiazole.
Abstract: Five aroylhydrazines have been oxidised by lead tetra-acetate, usually at room temperature, to give, after hydrolysis, high yields of the corresponding aroic acids. A study of the reaction of benzhydrazide under various conditions has provided evidence that reaction occurs by way of the aroyldi-imide, and this can be diverted in Part to give benzaldehyde and thence, by further reactions, 2,5-diphenyloxadiazole. When the hydrazide is in considerable excess, it can trap an intermediate in the oxidation to give NN′-dibenzoylhydrazine. The oxidation of benzhydrazide by mercuric acetate occurs in a similar manner, although not under such mild conditions.


Journal ArticleDOI
TL;DR: In this paper, the reactions of benzamidine with several aldehydes in the presence of hydrogen cyanide were studied, using an aqueous methanol as a solvent.
Abstract: The reactions of benzamidine with several aldehydes in the presence of hydrogen cyanide were studied, using an aqueous methanol as a solvent. When formaldehyde or acetaldehyde was used as an aldehyde component, α-hydroxyalkyldiphenyl-s-triazines were obtained, while when benzaldehyde, p-chlorobenzaldehyde, or furfural was used, the corresponding 4-arylmethylidenamino-2,5-diphenyloxazoles were obtained. However, under the same reaction conditions, m-nitrobenzaldehyde afforded dimethyl azoxybenzene-3,3′-dicarboxylate.


Journal ArticleDOI
TL;DR: Decarboxylation of 1, 2, 3, 4-tetrahydroisoquinoline-3-carboxylic acid derivatives, I, II, III, IV and IV hydrochloride, in acetophenone and benzaldehyde as solvents found that 4-substituted isoquinoline derivatives were formed in moderate yield according to the solvent used.
Abstract: Decarboxylation of 1, 2, 3, 4-tetrahydroisoquinoline-3-carboxylic acid derivatives, I, II, III, IV and IV hydrochloride, in acetophenone and benzaldehyde as solvents, was examined. It was found that in the case of IV hydrochloride, 4-substituted isoquinoline derivatives were formed in moderate yield according to the solvent used.

Journal ArticleDOI
TL;DR: In this article, peroxybenzoic acid was used to yield the 10-oxide, 2-(2-hydroxyanilino)benzaldehyde, and 2(2]-hydroxynilino (2-HOGO) acid, and NN′-oxydi-9acridone.
Abstract: Acridine reacted with peroxybenzoic acid to yield the 10-oxide, 2-(2-hydroxyanilino)benzaldehyde, and 2-(2-hydroxyanilino)benzoic acid. With 3-chloroperoxybenzoic acid, the 10-oxide, the aldehyde, and NN′-oxydi-9-acridone were obtained.

Patent
01 Aug 1968
TL;DR: The benzaldazine derivative is prepared by heating an alcoholic solution of the dodecyl ester of benzaldehyde carbonic acid in pyridine under reflux with hydrazine hydrate in the presence of glacial acetic acid as discussed by the authors.
Abstract: 1,198,337. Benzaldazine derivative. AGFAGEVAERT A.G. 1 Aug., 1968 [3 Aug., 1967], No. 36647/68. Heading C2C. [Also in Division G2] Di - (m - dodecylozycarbozy) benzaldazine is prepared by heating an alcoholic solution of the dodecyl ester of benzaldehyde carbonic acid, obtained by reacting 3-hydroxybenzaldehyde and chloroformic acid dodecyl ester in pyridine, under reflux with hydrazine hydrate in the presence of glacial acetic acid.



Journal ArticleDOI
TL;DR: The formation of a 2,3-O-monoacetal in the reaction of an aldehyde with D-glucitol in acid solution, first shown to occur with n-butyraldehyde, has now been observed with both benzaldehyde and acetaldehyde as discussed by the authors.
Abstract: The formation under kinetic control of a 2,3-O-monoacetal in the reaction of an aldehyde with D-glucitol in acid solution, first shown to occur with n-butyraldehyde, has now been observed with both benzaldehyde and acetaldehyde. Hydrolysis of the 2,3-O-ethylidene acetal in aqueous acid gives substantial fission of the acetal ring followed by recombination to the 2,4-acetal. The 2,3-O-benzylidene acetal appears to undergo ring migration to the 2,4-acetal in anhydrous media.

Journal ArticleDOI
TL;DR: Reaction of thiamine-sodium salt (IV) with benzaldehyde in the presence of carbon dioxide afforded 2-benzoyl-3-(2-methyl-4-aminopyrimidin-5-yl-methyl)-3a-methylperhydrofuro [2, 3-d] thiazole (Va), and stereochemistry of the product was discussed.
Abstract: Reaction of thiamine-sodium salt (IV) with benzaldehyde in the presence of carbon dioxide afforded 2-benzoyl-3-(2-methyl-4-aminopyrimidin-5-yl-methyl)-3a-methylperhydrofuro [2, 3-d] thiazole (Va) involving an unusual carbon-acylation at thiazole C-2 position of thiamine, and stereochemistry of the product was discussed Va was also obtained from reaction of thiamine hydrochloride (I) with benzaldehyde in the presence of triethylamine under anhydrous condition Some other aldehydes also reacted to furnish corresponding C-2 acylated thiamine derivatives

Journal ArticleDOI
TL;DR: In this article, the autoxidations of benzene, toluene and ethylbenzene were investigated at 70°C by using the oxygen-18 enriched Fenton's reagent.
Abstract: The autoxidations of benzene, toluene and ethylbenzene were investigated at 70°C by using the oxygen-18 enriched Fenton’s reagent. The oxygen-18 atom percentage in the products suggests that all the oxygen of benzaldehyde from toluene and of acetophenone from ethylbenzene is donated by molecular oxygen dissolved in the aqueous phase, while the oxygen of the hydroxylation products, namely, phenol from benzene, benzyl alcohol from toluene and methyl phenyl carbinol from ethylbenzene, is donated partly from water and partly from molecular oxygen. From the latter finding, the rate of the carbonium cation formation from the intermediate radicals without their oxidation to the peroxide is in the order of phenyl>α-methyl-benzyl>benzyl.

Patent
02 May 1968
TL;DR: In this article, a 2.2-(LOWER-ALKOXY)-2-PHENYLALKANENITRILE with an ALKANEDIAMINE, wherein 2,3 or 4 CARBON ATOMS, RESPECTIVELY INTERVENE BETWEEN the two AMINO GROUPS, in the PRESENCE of a CATalytic AMOUNT of CARbon Disulfide or HYDROGEN SULFIDE.
Abstract: 2-(A-(LOWER-ALKOXY) BENZYL) -2-IMIDZOLINES,-1,4,5,6TETRAHYDROPYRIMIDINES AND -4,5,6,7-TETRAHYDRO-1H-1,3-DIAZEPINES, HAVING PHARMACOLOGICAL PROPERTIES, E.G., HYPOGLYCEMIC, DIURETIC, ANTI-INFLAMMATORY, ARE PREPARED BY HEATING A 2-(LOWER-ALKOXY)-2-PHENYLALKANENITRILE WITH AN ALKANEDIAMINE, WHEREIN 2,3 OR 4 CARBON ATOMS, RESPECTIVELY INTERVENE BETWEEN THE TWO AMINO GROUPS, IN THE PRESENCE OF A CATALYTIC AMOUNT OF CARBON DISULFIDE OR HYDROGEN SULFIDE. THE INTERMEDIATE 2-(LOWER-ALKOXY)-2PHENYLALKANENITRILES ARE PREPARED PREFERABLY BY FIRST REACTING A BENZALDEHYDE WITH A TRI-(LOWER-ALKYL) ORTHOFORMATE TO FORM THE ALDEHYDE DI-(LOWER-ALKYL) ACETAL, REACTING THE LATTER WITH AN ACYL HALIDE TO FORM THE CORRESPONDING AHALOBENZYL LOWER-ALKYL ETHER AND REACTING SAID ETHER WITH AN ALKALI CYANIDE TO YIELD SAID INTERMEDIATE NITRILE.