Über die Einwirkung von Aluminiumchlorid auf Lösungen aromatischer Nitro‐kohlenwasserstoffe in aromatischen Kohlenwasserstoffen

Kliegl, A.; Huber, Hanspeter

doi:10.1002/cber.19200530907

Cited by 18 publications

(7 citation statements)

References 2 publications

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“…42-43') and 4-acetamido-3 : 4'-dimethyldiphenyl (m.p. 206') reported by Kliegl & Huber (1920). The amine was shown to be 4-amino-3 : 3'-dimethyldiphenyl by deamination and oxidation of the resulting dimethyldiphenyl to diphenyl-3 : 3'-dicarboxylic acid, and this structure was confirmed by its synthesis from 4'-acetamido-+amin0-3 : 3'-dimethyldiphenyl by deaminating and hydrolysing the resulting 4-acetamido-3 : 3'-dimethyldiphenyl.…”

Section: Introductionmentioning

confidence: 85%

The orienting influence of the methyl group in toluene in the gomberg reaction

Wilson¹

1953

J. Appl. Chem.

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When diazotized 6‐nitro‐m‐toluidine (Me = 1) reacts with toluene, substitution occurs in the ortho‐and meta‐positions in the toluene, to give 3:2′‐dimethyl‐4‐nitrodiphenyl and 3: 3′‐dimethyl‐4‐nitrodiphenyl. The proportion of meta‐substitution is greater than that observed in electrophilic substitutionreactions with toluene, confirming conclusions drawn from the quantum‐mechanical analysis of Wheland (1942).

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Section: Introductionmentioning

confidence: 85%

The orienting influence of the methyl group in toluene in the gomberg reaction

Wilson¹

1953

J. Appl. Chem.

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“…Beziiglich der Umsetzung von Phenylhydroxylamin und Arylaziden in aromatischen Kohlenwasserstoffen in Gegenwart von Aluminiumchlorid vgl. [7] IS]. Kurzlich wurde auch die photochemische Zersetzung von Arylaziden in Gegenwart von aromatischen Verbindungen und Trifluoressigsaure beschrieben [9].…”

Section: $'unclassified

“…8, Schema I ) . Kliegl & Huher [7] erhielten aus Phenylhydroxylarnin und Toluol mit Aluminiumchlorid 5% 4-Methyl-diphenylamin und 6,5% 4-Amino-4'-methyl-biphenyl. Borsche & Hahn [8] isolierten aus einem gleichartigen Versuch 35% des Diphenylamins und 22% Anilin als Reduktionsprodukt.…”

Section: Schemaunclassified

“…Phenylhydroxylamin und Anisol ergaben nach [8] rnit Aluminiumchlorid 35% 4-Methoxy-diphenylamin; ein entsprechendes Biphenylderivat wurde nicht beobachtet. Aus Phenylhydroxylamin und Benzol bildeten sich neben Spuren von Anilin 4-Amino-biphenyl und 4-Aminophenol [7]; im Kontrollversuch wurde aus letzterem und Benzol kein 4-Amino-biphenyl erhalten [7]. Phenylhydroxylamin ergab rnit Phenol in wasseriger 25proz.…”

Section: Schemaunclassified

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Photolyse von 3‐Methyl‐2, 1‐benzisoxazol (3‐Methylanthranil) und 2‐Azido‐acetophenon in Gegenwart von Schwefelsäure und Benzolderivaten

Doppler

Schmid

Hansen

1979

Helvetica Chimica Acta

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Photolysis of 3‐Methyl‐2, 1‐benzisoxazole (3‐Methylanthranil) and 2‐Azido‐acetophenone in the Presence of Sulfuric Acid and Benzene Derivatives Irradiation of 3‐methylanthranil (1) in acetonitrile in the presence of sulfuric acid and benzene, toluene, p‐xylene, mesitylene or anisole with a mercury high‐pressure lamp through a pyrex filter yields beside varying amounts of 2‐amino‐acetophenone (3) and 2‐amino‐5‐hydroxy‐ (4a) and 2‐amino‐3‐hydroxy‐acetophenone (4b) the corresponding diphenylamine derivatives 5 (see Table 1). In the case of toluene and anisole mixtures of the corresponding ortho‐ and para‐substituted isomers (5b, 5d or 5g, 5i respectively), but no meta‐substituted isomers (5c or 5h) are obtained. In addition to these products, the irradiation of 1 in the presence of anisole yields also 2‐amino‐5‐(4′‐methoxyphenyl)‐acetophenone (7), 2‐amino‐3‐(4′‐methoxyphenyl)‐acetophenone (8) and 2‐methoxy‐9‐methyl‐acridine (6; see Scheme 1). The latter product is also formed thermally by acid catalysis from the diphenylamine derivative 5i. Irradiation of 2‐azido‐acetophenone (2) in acetonitrile solution in the presence of sulfuric acid and benzene leads to the formation of 1, 3, 4a, 4b, 5a and 9 (see Table 2). Compounds 3, 4a, 4b and 5a are also obtained after acid catalyzed decomposition of 2 in the presence of benzene. Thus, it is concluded that irradiation of 1 or 2 in the presence of sulfuric acid yields 2‐acetyl‐phenylnitrenium ions 10 in the singlet ground state which will undergo electrophilic substitution of the aromatic compounds, perhaps via the π‐complex 11 (see Scheme 2).

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“…References: ^omberg (1900); 2 Hodgson and Marsden (1940); 3 Grieve and Hey (1934); 4 Elks and Hey (1943); 5 Grieve and Hey (1932); 6 Case (1938); 7 France, Heilbron and Hey (1938); 8 Elks, Haworth and Hey (1940); 9 Hey and Lawton (1940); 10 Hey (1934); n Butterworth, Heilbron, Hey and Wilkinson (1938); 12 Heilbron, Hey and Wilkinson (1938); 13 Gomberg and Pernert (1926); 14 Möhlau and Berger (1893b); 15 Wieland, Popper and Seefried (1922); ie Bamberger (1895); 17 Bamberger (1896); 18 Franc^ Heilbron and Hey (1939); 19 Kliegl and Huber (1920); 20 Kuhling (1895Kuhling ( , 1896; 21 Dietrich (1925); 22 Lippmann (1886); 23 Hey (1932); 24 Dunstan and Hughes (1946); 25 Harley-Mason and Mann (1940); 26 Gomberg and Bachmann (1924); 27 Hey and Walker (1948); 28 Haworth, Heilbron and Hey (1940a); 29 Haworth, Heilbron and Hey (1940b); 30 Wieland and co-workers (1930Wieland and co-workers ( , 1934...…”

Section: Reaction Mechanismmentioning

confidence: 99%

Quantitative Investigation of Homolytic Arylation

Williams¹

1960

Homolytic Aromatic Substitution

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Über die Einwirkung von Aluminiumchlorid auf Lösungen aromatischer Nitro‐kohlenwasserstoffe in aromatischen Kohlenwasserstoffen

Cited by 18 publications

References 2 publications

The orienting influence of the methyl group in toluene in the gomberg reaction

The orienting influence of the methyl group in toluene in the gomberg reaction

Photolyse von 3‐Methyl‐2, 1‐benzisoxazol (3‐Methylanthranil) und 2‐Azido‐acetophenon in Gegenwart von Schwefelsäure und Benzolderivaten

Quantitative Investigation of Homolytic Arylation

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