Acid-catalyzed solvolysis of N-sulfonyl-and N-acyl-O-arylhydroxylamines. Phenoxenium ions

Y Endo, K Shudo, T Okamoto

Index: Endo, Yasuyuki; Shudo, Koichi; Okamoto, Toshihiko Journal of the American Chemical Society, 1982 , vol. 104, # 23 p. 6393 - 6397

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Citation Number: 54

Abstract

Abstract: The acid-catalyzed reaction of N-acyl-and N-sulfonyl-Oarylhydroxylamines with benzene proceeded quite smoothly to give 2-and 4-hydroxybiphenyls, The results of product analysis, the orientation of the reaction, and the effects of substituents on the nitrogen atom and on the phenyl ring suggested a mechanism that involves a phenoxenium ion. The phenoxenium ion was trapped by benzene and other various nucleophiles.

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Ethyl N-hydroxyacetimidate Structure

10576-12-2

Ethyl N-hydroxy...

1-Fluoro-4-nitrobenzene Structure

350-46-9

1-Fluoro-4-nitr...

~51%

ethyl N-(4-nitrophenoxy)ethanimidate Structure

83077-00-3

ethyl N-(4-nitr...

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O-(4-methylphenyl)hydroxylamine Structure

65440-81-5

O-(4-methylphen...

Tosyl chloride Structure

98-59-9

Tosyl chloride

~%

4-methyl-N-(4-methylphenoxy)benzenesulfonamide Structure

65109-76-4

4-methyl-N-(4-m...

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phenoxy-amine Structure

4846-21-3

phenoxy-amine

~%

(4-hydroxyphenyl) trifluoromethanesulfonate Structure

65109-80-0

(4-hydroxypheny...

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N/A Structure

65109-75-3

N/A

~0%

2-hydroxyphenyl p-toluenesulfonimidate Structure

65109-81-1

2-hydroxyphenyl...

(4-hydroxyphenyl) trifluoromethanesulfonate Structure

65109-80-0

(4-hydroxypheny...

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Trifluoromethanesulfonic acid Structure

1493-13-6

Trifluoromethan...

N/A Structure

65109-75-3

N/A

~0%

2-hydroxyphenyl p-toluenesulfonimidate Structure

65109-81-1

2-hydroxyphenyl...

(4-hydroxyphenyl) trifluoromethanesulfonate Structure

65109-80-0

(4-hydroxypheny...

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2,2,2-Trifluoroethanol Structure

75-89-8

2,2,2-Trifluoro...

N/A Structure

65109-75-3

N/A

~8%

2-hydroxyphenyl p-toluenesulfonimidate Structure

65109-81-1

2-hydroxyphenyl...

4-(2,2,2-trifluoroethoxy)phenol Structure

129560-99-2

4-(2,2,2-triflu...

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N/A Structure

65109-75-3

N/A

acetic acid Structure

64-19-7

acetic acid

~16%

1,2-Benzenediol,1-acetate Structure

2848-25-1

1,2-Benzenediol...

4-Acetoxyphenol Structure

3233-32-7

4-Acetoxyphenol

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N/A Structure

65109-75-3

N/A

benzene Structure

71-43-2

benzene

~3%

4-Biphenylol Structure

92-69-3

4-Biphenylol

2-hydroxyphenyl p-toluenesulfonimidate Structure

65109-81-1

2-hydroxyphenyl...

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N/A Structure

65109-75-3

N/A

Anisole Structure

100-66-3

Anisole

~15%

2-(4-methoxyphenyl)phenol Structure

21849-91-2

2-(4-methoxyphe...

2-(2-methoxyphenyl)phenol Structure

3594-88-5

2-(2-methoxyphe...

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N/A Structure

65109-75-3

N/A

Anisole Structure

100-66-3

Anisole

~18%

2-(4-methoxyphenyl)phenol Structure

21849-91-2

2-(4-methoxyphe...

2-(2-methoxyphenyl)phenol Structure

3594-88-5

2-(2-methoxyphe...

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4-methyl-N-(4-methylphenoxy)benzenesulfonamide Structure

65109-76-4

4-methyl-N-(4-m...

benzene Structure

71-43-2

benzene

~43%

2,2'-dihydroxy-5,5'-dimethyl-m-terphenyl Structure

65109-83-3

2,2'-dihydroxy-...

4-methyl-2-phenyl-phenol Structure

39579-09-4

4-methyl-2-phen...

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N/A Structure

65109-75-3

N/A

Phenol Structure

108-95-2

Phenol

~32%

biphenol Structure

1806-29-7

biphenol

4,4'-Dihydroxybiphenyl Structure

92-88-6

4,4'-Dihydroxyb...

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phenoxy-amine Structure

4846-21-3

phenoxy-amine

~%

[1,1-Biphenyl]-2,4-diol Structure

611-62-1

[1,1-Biphenyl]-...

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O-phenylbenzohydroxamic acid Structure

4380-77-2

O-phenylbenzohy...

~75%

o-hydroxyphenyl benzoate Structure

5876-92-6

o-hydroxyphenyl...

Benzamide Structure

55-21-0

Benzamide

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O-phenylbenzohydroxamic acid Structure

4380-77-2

O-phenylbenzohy...

~0%

o-hydroxyphenyl benzoate Structure

5876-92-6

o-hydroxyphenyl...

Benzamide Structure

55-21-0

Benzamide

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N/A Structure

65109-75-3

N/A

acetic acid Structure

64-19-7

acetic acid

~0%

1,2-Benzenediol,1-acetate Structure

2848-25-1

1,2-Benzenediol...

4-Acetoxyphenol Structure

3233-32-7

4-Acetoxyphenol

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phenoxy-amine Structure

4846-21-3

phenoxy-amine

~%

2-(ETHYLTHIO)PHENOL Structure

29549-60-8

2-(ETHYLTHIO)PHENOL

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1-(Aminooxy)-4-nitrobenzene Structure

33543-55-4

1-(Aminooxy)-4-...

~%

5-Nitro-2-biphenylol Structure

4291-29-6

5-Nitro-2-biphenylol

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ethyl N-(4-nitrophenoxy)ethanimidate Structure

83077-00-3

ethyl N-(4-nitr...

~%

5-Nitro-2-biphenylol Structure

4291-29-6

5-Nitro-2-biphenylol

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1-Fluoro-4-nitrobenzene Structure

350-46-9

1-Fluoro-4-nitr...

~%

5-Nitro-2-biphenylol Structure

4291-29-6

5-Nitro-2-biphenylol

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N-(4'-nitrophenoxy)-4-methylbenzenesulfonamide Structure

83076-99-7

N-(4'-nitrophen...

benzene Structure

71-43-2

benzene

~41%

5-Nitro-2-biphenylol Structure

4291-29-6

5-Nitro-2-biphenylol

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N/A Structure

65109-75-3

N/A

Anisole Structure

100-66-3

Anisole

~15%

2-(4-methoxyphenyl)phenol Structure

21849-91-2

2-(4-methoxyphe...

2-(2-methoxyphenyl)phenol Structure

3594-88-5

2-(2-methoxyphe...

Detail Learn More

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