e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521

Acid-catalyzed reactions of N-arylhydroxylamines and related compounds with benzene. Iminium-benzenium ions

K Shudo, T Ohta, T Okamoto

Index: Shudo, Koichi; Ohta, Toshiharu; Okamoto, Toshihiko Journal of the American Chemical Society, 1981 , vol. 103, # 3 p. 645 - 653

Full Text: HTML

Citation Number: 47

Abstract

Abstract: N-Arylhydroxylamines react with benzene in the presence of trifluoroacetic acid (TFA) at room temperature to give diphenylamines. When TFA was replaced by a strong acid, trifluoromethanesulfonic acid (TFSA), the major products were aminobiphenyls. The nature of the reaction was explored by reactions of 4-substituted phenylhydroxylamines and dialkylaniline N-oxides with benzene. Thus, it was demonstrated that the reactive ...

N-Phenylhydroxylamine Structure

N-Phenylhydroxy...

~0%

4-Methoxydiphenylamine Structure

4-Methoxydiphen...

2-methoxy-N-phenylaniline Structure

2-methoxy-N-phe...

fentoxan Structure

4-chlorophenylhydroxylamine Structure

4-chlorophenylh...

~%

N-(4-chloro-2-phenyl-phenyl)acetamide Structure

N-(4-chloro-2-p...

benzene Structure

~%

N-(4-chloro-2-phenyl-phenyl)acetamide Structure

N-(4-chloro-2-p...

1-Iodo-4-nitrobenzene Structure

1-Iodo-4-nitrob...

~%

4-(3-methylphenyl)aniline Structure

4-(3-methylphen...

3-Iodotoluene Structure

~%

4-(3-methylphenyl)aniline Structure

4-(3-methylphen...

N-Phenylhydroxylamine Structure

N-Phenylhydroxy...

Toluene Structure

~9%

4'-Methyl-4-biphenylamine hydrochloride (1:1) Structure

4'-Methyl-4-bip...

4AMINO2METHYLBIPHENYL Structure

4AMINO2METHYLBI...

Detail

N-Phenylhydroxylamine Structure

N-Phenylhydroxy...

Toluene Structure

~9%

2-(4-methylphenyl)aniline Structure

2-(4-methylphen...

4AMINO2METHYLBIPHENYL Structure

4AMINO2METHYLBI...

Detail

N,N-dimethylaniline N-oxide Structure

N,N-dimethylani...

~7%

[1,1'-Biphenyl]-4-amine,N,N-dimethyl- Structure

[1,1'-Biphenyl]...

N,N-dimethyl-[1,1'-biphenyl]-2-amine Structure

N,N-dimethyl-[1...

2-Dimethylaminophenol Structure

2-Dimethylamino...

N,N-dimethylaniline N-oxide Structure

N,N-dimethylani...

benzene Structure

~72%

[1,1'-Biphenyl]-4-amine,N,N-dimethyl- Structure

[1,1'-Biphenyl]...

N,N-dimethyl-[1,1'-biphenyl]-2-amine Structure

N,N-dimethyl-[1...

4-chlorophenylhydroxylamine Structure

4-chlorophenylh...

benzene Structure

~44%

[1,1':2',1''-Terphenyl]-4'-amine Structure

[1,1':2',1''-Te...

[1,1':3',1''-Terphenyl]-4'-amine Structure

[1,1':3',1''-Te...

Detail

1-Iodo-4-nitrobenzene Structure

1-Iodo-4-nitrob...

3-Iodotoluene Structure

~%

3-Methyl-4'-nitro-1,1'-biphenyl Structure

3-Methyl-4'-nit...

N-Phenylhydroxylamine Structure

N-Phenylhydroxy...

Toluene Structure

~17%

4'-Methyl-4-biphenylamine hydrochloride (1:1) Structure

4'-Methyl-4-bip...

4AMINO2METHYLBIPHENYL Structure

4AMINO2METHYLBI...

Detail

N-Phenylhydroxylamine Structure

N-Phenylhydroxy...

Toluene Structure

~18%

2-(4-methylphenyl)aniline Structure

2-(4-methylphen...

4AMINO2METHYLBIPHENYL Structure

4AMINO2METHYLBI...

Detail

4-(HYDROXYAMINO)TOLUENE Structure

4-(HYDROXYAMINO...

benzene Structure

~37%

4-Aminodiphenylmethane Structure

4-Aminodiphenyl...

2-Amino-5-methylbiphenyl Structure

2-Amino-5-methy...

Detail

N-Phenylhydroxylamine Structure

N-Phenylhydroxy...

~39%

4-Methoxydiphenylamine Structure

4-Methoxydiphen...

2-methoxy-N-phenylaniline Structure

2-methoxy-N-phe...

fentoxan Structure

4-(HYDROXYAMINO)TOLUENE Structure

4-(HYDROXYAMINO...

~64%

(4-Methoxy-phenyl)-p-tolyl-amine Structure

(4-Methoxy-phen...

Diazene,1,2-bis(4-methylphenyl)- Structure

Diazene,1,2-bis...

4-(HYDROXYAMINO)TOLUENE Structure

4-(HYDROXYAMINO...

Anisole Structure

~64%

(4-Methoxy-phenyl)-p-tolyl-amine Structure

(4-Methoxy-phen...

Diazene,1,2-bis(4-methylphenyl)- Structure

Diazene,1,2-bis...

m-Terphenyl Structure

~%

[1,1':3',1''-Terphenyl]-4'-amine Structure

[1,1':3',1''-Te...

fentoxan Structure

benzene Structure

~3%

[1,1':2',1''-Terphenyl]-4'-amine Structure

[1,1':2',1''-Te...

[1,1':3',1''-Terphenyl]-4'-amine Structure

[1,1':3',1''-Te...

Detail

Nitrosobenzene Structure

benzene Structure

~27%

[1,1':2',1''-Terphenyl]-4'-amine Structure

[1,1':2',1''-Te...

[1,1':3',1''-Terphenyl]-4'-amine Structure

[1,1':3',1''-Te...

Detail

4-Hydroxyaminobiphenyl Structure

4-Hydroxyaminob...

benzene Structure

~17%

4-Amino-p-terphenyl Structure

4-Amino-p-terphenyl

[1,1':2',1''-Terphenyl]-4'-amine Structure

[1,1':2',1''-Te...

Detail

N-(4-methoxyphenyl)hydroxylamine Structure

N-(4-methoxyphe...

benzene Structure

~2%

4-methoxy-2-phenylaniline Structure

4-methoxy-2-phe...

[1,1':2',1''-Terphenyl]-4'-amine Structure

[1,1':2',1''-Te...

Detail

1,2-diphenyldiazene Structure

1,2-diphenyldiazene

benzene Structure

~3%

[1,1':2',1''-Terphenyl]-4'-amine Structure

[1,1':2',1''-Te...

[1,1':3',1''-Terphenyl]-4'-amine Structure

[1,1':3',1''-Te...

Detail

4-chlorophenylhydroxylamine Structure

4-chlorophenylh...

benzene Structure

~1%

[1,1':2',1''-Terphenyl]-4'-amine Structure

[1,1':2',1''-Te...

[1,1':3',1''-Terphenyl]-4'-amine Structure

[1,1':3',1''-Te...

Detail

Nitrosobenzene Structure

benzene Structure

~3%

[1,1':2',1''-Terphenyl]-4'-amine Structure

[1,1':2',1''-Te...

[1,1':3',1''-Terphenyl]-4'-amine Structure

[1,1':3',1''-Te...

Detail

fentoxan Structure

benzene Structure

~1%

[1,1':2',1''-Terphenyl]-4'-amine Structure

[1,1':2',1''-Te...

[1,1':3',1''-Terphenyl]-4'-amine Structure

[1,1':3',1''-Te...

Detail

Nitrosobenzene Structure

benzene Structure

~2%

[1,1':2',1''-Terphenyl]-4'-amine Structure

[1,1':2',1''-Te...

[1,1':3',1''-Terphenyl]-4'-amine Structure

[1,1':3',1''-Te...

Detail

4-Hydroxyaminobiphenyl Structure

4-Hydroxyaminob...

benzene Structure

~3%

4-Amino-p-terphenyl Structure

4-Amino-p-terphenyl

[1,1':2',1''-Terphenyl]-4'-amine Structure

[1,1':2',1''-Te...

Detail

N-(4-methoxyphenyl)hydroxylamine Structure

N-(4-methoxyphe...

benzene Structure

~3%

4-methoxy-2-phenylaniline Structure

4-methoxy-2-phe...

[1,1':2',1''-Terphenyl]-4'-amine Structure

[1,1':2',1''-Te...

Detail

1,2-diphenyldiazene Structure

1,2-diphenyldiazene

benzene Structure

~1%

[1,1':2',1''-Terphenyl]-4'-amine Structure

[1,1':2',1''-Te...

[1,1':3',1''-Terphenyl]-4'-amine Structure

[1,1':3',1''-Te...

Detail

4-chlorophenylhydroxylamine Structure

4-chlorophenylh...

benzene Structure

~1%

[1,1':2',1''-Terphenyl]-4'-amine Structure

[1,1':2',1''-Te...

[1,1':3',1''-Terphenyl]-4'-amine Structure

[1,1':3',1''-Te...

Detail

3-nitrobiphenyl Structure

3-nitrobiphenyl

benzene Structure

~%

[1,1':2',1''-Terphenyl]-4'-amine Structure

[1,1':2',1''-Te...

Nitrosobenzene Structure

benzene Structure

~0%

[1,1':2',1''-Terphenyl]-4'-amine Structure

[1,1':2',1''-Te...

[1,1':3',1''-Terphenyl]-4'-amine Structure

[1,1':3',1''-Te...

Detail

4-(HYDROXYAMINO)TOLUENE Structure

4-(HYDROXYAMINO...

benzene Structure

~24%

4-Aminodiphenylmethane Structure

4-Aminodiphenyl...

2-Amino-5-methylbiphenyl Structure

2-Amino-5-methy...

Detail

N,N-dimethylaniline N-oxide Structure

N,N-dimethylani...

~0%

[1,1'-Biphenyl]-4-amine,N,N-dimethyl- Structure

[1,1'-Biphenyl]...

N,N-dimethyl-[1,1'-biphenyl]-2-amine Structure

N,N-dimethyl-[1...

2-Dimethylaminophenol Structure

2-Dimethylamino...

1-Iodo-4-nitrobenzene Structure

1-Iodo-4-nitrob...

4-Iodotoluene Structure

~%

4-METHYL-4'-NITRO-1,1'-BIPHENYL Structure

4-METHYL-4'-NIT...

N-Phenylhydroxylamine Structure

N-Phenylhydroxy...

Toluene Structure

~0%

4'-Methyl-4-biphenylamine hydrochloride (1:1) Structure

4'-Methyl-4-bip...

4AMINO2METHYLBIPHENYL Structure

4AMINO2METHYLBI...

Detail

N-Phenylhydroxylamine Structure

N-Phenylhydroxy...

Toluene Structure

~0%

2-(4-methylphenyl)aniline Structure

2-(4-methylphen...

4AMINO2METHYLBIPHENYL Structure

4AMINO2METHYLBI...

Detail

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