Über die Kupplung der Phenole und Phenoläther mit Diazoverbindungnen

Meyer, Kurt H.; Irschick, Alfred; Schlösser, Hans

doi:10.1002/cber.19140470263

Cited by 37 publications

(10 citation statements)

References 4 publications

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“…All reaction products are known compounds. For spectral comparison and analytic purposes, authentic samples were prepared as described: 2a 10 , 3a 16 , 4a 17 , 5a 18 10: δ 6.69 (H-3), 2.50 (CH 3 ); 11 δ 6.82 (H-3), 2.61 (CH 3 ). There was no interference by foreign peaks as the catalysts remained in the aqueous phase or were removed as described below.…”

Section: Methodsmentioning

confidence: 99%

Regioselective Alkylation of Anthrone, 5,5-dimethyl-3-isoxazolidinone and 4-methylquinolone by phase transfer catalysis

Dehmlow

Bollhöfer

Thye

2001

Journal of Chemical Research

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Anthrone (1) can be alkylated selectively to give O-, C,O- or C,C-substituted compounds 2, 4, or 5, respectively. Similarly, 5,5-dimethyl-3-isoxazolidinone (6) and 4-methylquinolone (9) yield N- or O-derivatives 7 and 8 or 10 and 11, respectively. The product ratios can be influenced strongly sometimes by use of different phase transfer catalysts, but the sensitivity of each reaction towards the catalysts is unique.

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Section: Methodsmentioning

confidence: 99%

Regioselective Alkylation of Anthrone, 5,5-dimethyl-3-isoxazolidinone and 4-methylquinolone by phase transfer catalysis

Dehmlow

Bollhöfer

Thye

2001

Journal of Chemical Research

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“…3-Trimethylsilyl-and 3-triphenylsilyl-2-methoxynaphthalene, however, did not couple with p-nitrobenzenediazonium chloride, although 2-methoxynapthhalene has been reported to couple with p-nitrobenzenediazonium chloride (13). Only the dyes from sulfanilic acid could not be obtained in pure form due to their high solubilities in water.…”

Section: Sunth4nkar and Henry Gilmanmentioning

confidence: 96%

“…Only the dyes from sulfanilic acid could not be obtained in pure form due to their high solubilities in water. 3-TrimethyIsilyl-and 3-triphenylsilyl-2-methoxynaphthalene, however, did not couple with p-nitrobenzenediazonium chloride, although 2-methoxynapthhalene has been reported to couple with p-nitrobenzenediazonium chloride (13).…”

mentioning

confidence: 88%

Silicon-Containing Azo Dyes

Sunthankar¹,

Gilman²

1950

J. Org. Chem.

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The relation between chemical constitution and the carcinogenic action of the azo dyes has not been as extensively investigated as in the case of polynuclear hydrocarbons. However, from the studies of the carcinogenic action of p-aminoazobenzene and its derivatives, it was found that methyl groups greatly enhance the potency of the parent azo dye, provided these groups occupy certain positions. For example, 4-N ,N-dimethylaminoaaobenzene (I) and its 2'-, 3'-, and 4'-methyl derivatives as well as 2-methyl-and 2 , 2'-dimethyl derivatives were found to possess carcinogenic potency (1). It was, therefore, thought to be of Ha C' I interest to study the carcinogenic action of some trimethylsilyl and triphenylsilyl derivatives of (I), to compare the effect of an RsSi group with a methyl group from the point of view of carcinogenic potency of the respective azo dyes. The second purpose was to examine the substantivity of these dyes for textile fibers, in order to find out if the substitution of the R3Si group has any favorable effect on their substantivity. We, therefore, have synthesized several siliconcontaining azo dyes, which are reported in this paper. The only silicon-containing azo compound reported in the literature is 4 ,4-' bis(triethylsilyl)azobenzene, obtained by the reduction of 4-nitrophenyltriethylsilane with zinc and sodium hydroxide (2).The preparation of the trimethylsilyl and triphenylsilyl derivatives of (I) met with certain difficulties. For example, attempts to prepare derivatives of (I) with an R3Si group in the benzene ring B have not been successful. The reaction of organolithium derivatives of aniline with the appropriate chlorosilanes yielded polymeric products rather than the trimethylsilyl-and triphenylsilylaniline required for coupling with dimethylaniline. Furthermore, the reduction of p-nitrophenyltrimethylsilane with hydrogen under pressure using Raney nickel as a catalyst is reported to give only a low over-all yield of the corresponding amine.' Therefore, our preliminary study was restricted to the preparation of dyes having an RsSi-substituent in the benzene ring A. The silicon-containing azo dyes were prepared by coupling organosilicon compounds with selected diazonium salts. The organosilicon compounds were synthesized by the action of trimethylsilyl chloride and triphenylsilyl chloride Unpublished studies by Dr. R. A. Benkeser. 1200

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“…A. With DMSO-DCC.-A solution of 23 (1.84 g, 10 mmol), DCC (5.8 g, 28 mmol), and anhydrous phosphoric acid was allowed to react in DMSO (5 ml) and benzene (5 ml) for 4 hr and then worked up with ethyl acetate. Preparative tic using two developments with CC14-CHClg (4:1) gave essentially a single product that was eluted giving 1.72 g (94%) of crystalline azobenzene (25) with mp 68-69°and .…”

Section: Reaction Of 24-dinitrophenylhydrazine (11)mentioning

confidence: 99%

Carbodiimide-sulfoxide reactions. XIII. Reactions of amines and hydrazine derivatives

Moffatt¹,

Lerch²

1971

J. Org. Chem.

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mechanisms cannot apply generally, of course, since a mobile group such as hydrogen is essential. Realistically, we believe we are left with steps a or c and i in Scheme I as alternate mechanisms in this system.Rate Comparisons.-In Table II we have collected rate data for Menschutkin substitutions of differing types of organic bromides. Were it necessary, one could estimate the rate constant for triethylamine with ethyl bromide in DMF.1816 It should be appreciated that any comparison of reactivity of saturated with unsaturated centers involves a comparison of an Sn2 with an Adx2 process. Our preliminary and generally qualitative comparisons6 stand up here: k (alkyl) fc (ethynyl) » k (vinyl) » k (aryl).

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Über die Kupplung der Phenole und Phenoläther mit Diazoverbindungnen

Cited by 37 publications

References 4 publications

Regioselective Alkylation of Anthrone, 5,5-dimethyl-3-isoxazolidinone and 4-methylquinolone by phase transfer catalysis

Regioselective Alkylation of Anthrone, 5,5-dimethyl-3-isoxazolidinone and 4-methylquinolone by phase transfer catalysis

Silicon-Containing Azo Dyes

Carbodiimide-sulfoxide reactions. XIII. Reactions of amines and hydrazine derivatives

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