Tetrahedron

Aromatic tertiary amines and n-butyl nitrite

G Verardo, AG Giumanini, P Strazzolini

Index: Varardo, Giancarlo; Giumanini, Angelo G.; Strazzolini, Paolo Tetrahedron, 1990 , vol. 46, # 12 p. 4303 - 4332

Full Text: HTML

Citation Number: 16

Abstract

The reaction between alkyl nitrites, particularly n-butyl nitrite, and tertiary aromatic amines under a variety of experimental conditions promptly yielded products of N-dealkylation-N- nitrosation, ring nitration, ipso-substitution and, occasionally, combinations of these processes. Aminoethers were detected as final products and intermediates on the way to N- nitrosations. Reaction pathways are suggested for some of the observed behaviours on ...

 Related Synthetic Route
N,N-Dimethylaniline Structure

121-69-7

N,N-Dimethylaniline

~4%

n-nitroso-n-methylaniline Structure

614-00-6

n-nitroso-n-met...

N,N-Dimethyl-4-[[4-(methylamino)phenyl]methyl]benzenamine Structure

53477-27-3

N,N-Dimethyl-4-...

N/A Structure

53477-25-1

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N,N-Dimethylaniline Structure

121-69-7

N,N-Dimethylaniline

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N-methyl-N,4-dinitrosoaniline Structure

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n-nitroso-n-methylaniline Structure

614-00-6

n-nitroso-n-met...

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4-Bromo-N,N-dimethylaniline Structure

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4-Bromo-N,N-dim...

~89%

Butane,1,1'-[methylenebis(oxy)]bis Structure

2568-90-3

Butane,1,1'-[me...

N-(4-bromophenyl)-N-methylnitrous amide Structure

937-23-5

N-(4-bromopheny...

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Butyl nitrite Structure

544-16-1

Butyl nitrite

4-Bromo-N,N-dimethylaniline Structure

586-77-6

4-Bromo-N,N-dim...

~88%

Butane,1,1'-[methylenebis(oxy)]bis Structure

2568-90-3

Butane,1,1'-[me...

N-(4-bromophenyl)-N-methylnitrous amide Structure

937-23-5

N-(4-bromopheny...

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4-Bromo-N,N-dimethylaniline Structure

586-77-6

4-Bromo-N,N-dim...

~58%

2,4-dibromo-N,N-dimethylaniline Structure

64230-27-9

2,4-dibromo-N,N...

4-Bromo-N,N-dimethyl-2-nitroaniline Structure

829-02-7

4-Bromo-N,N-dim...

N,N-DIMETHYL-4-NITROANILINE Structure

100-23-2

N,N-DIMETHYL-4-...

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Butyl nitrite Structure

544-16-1

Butyl nitrite

4-Bromo-N,N-dimethylaniline Structure

586-77-6

4-Bromo-N,N-dim...

~78%

Formaldehyde Structure

50-00-0

Formaldehyde

Butane,1,1'-[methylenebis(oxy)]bis Structure

2568-90-3

Butane,1,1'-[me...

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Butyl nitrite Structure

544-16-1

Butyl nitrite

4-Bromo-N,N-dimethylaniline Structure

586-77-6

4-Bromo-N,N-dim...

~20%

Butane,1,1'-[methylenebis(oxy)]bis Structure

2568-90-3

Butane,1,1'-[me...

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130717-77-0

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Butyl nitrite Structure

544-16-1

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586-77-6

4-Bromo-N,N-dim...

~0%

4-Bromo-N-(n-butoxymethyl)-N-methylbenzeneamine Structure

130717-77-0

4-Bromo-N-(n-bu...

4-Bromo-N,N-di(n-butoxymethyl)benzeneamine Structure

130717-78-1

4-Bromo-N,N-di(...

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4-methoxy-N,N-dimethylaniline Structure

701-56-4

4-methoxy-N,N-d...

~81%

Butane,1,1'-[methylenebis(oxy)]bis Structure

2568-90-3

Butane,1,1'-[me...

4-methoxy-N,N-dimethyl-2-nitroaniline Structure

60049-83-4

4-methoxy-N,N-d...

N/A Structure

130717-81-6

N/A

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Butyl nitrite Structure

544-16-1

Butyl nitrite

4-methoxy-N,N-dimethylaniline Structure

701-56-4

4-methoxy-N,N-d...

~86%

Butane,1,1'-[methylenebis(oxy)]bis Structure

2568-90-3

Butane,1,1'-[me...

4-methoxy-N,N-dimethyl-2-nitroaniline Structure

60049-83-4

4-methoxy-N,N-d...

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Butyl nitrite Structure

544-16-1

Butyl nitrite

4-methoxy-N,N-dimethylaniline Structure

701-56-4

4-methoxy-N,N-d...

~29%

N-(4-methoxyphenyl)-N-methylnitrous amide Structure

940-11-4

N-(4-methoxyphe...

4-methoxy-N,N-dimethyl-2-nitroaniline Structure

60049-83-4

4-methoxy-N,N-d...

Detail Learn More
4-Bromo-N,N-dimethylaniline Structure

586-77-6

4-Bromo-N,N-dim...

~6%

2,4-dibromo-N,N-dimethylaniline Structure

64230-27-9

2,4-dibromo-N,N...

4-Bromo-N,N-dimethyl-2-nitroaniline Structure

829-02-7

4-Bromo-N,N-dim...

N,N-DIMETHYL-4-NITROANILINE Structure

100-23-2

N,N-DIMETHYL-4-...

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Butyl nitrite Structure

544-16-1

Butyl nitrite

4-Bromo-N,N-dimethylaniline Structure

586-77-6

4-Bromo-N,N-dim...

~0%

Formaldehyde Structure

50-00-0

Formaldehyde

Butane,1,1'-[methylenebis(oxy)]bis Structure

2568-90-3

Butane,1,1'-[me...

Detail Learn More
N,N-Dimethylaniline Structure

121-69-7

N,N-Dimethylaniline

~0%

N-methyl-N,4-dinitrosoaniline Structure

99-80-9

N-methyl-N,4-di...

n-nitroso-n-methylaniline Structure

614-00-6

n-nitroso-n-met...

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Butyl nitrite Structure

544-16-1

Butyl nitrite

4-methoxy-N,N-dimethylaniline Structure

701-56-4

4-methoxy-N,N-d...

~66%

Butane,1,1'-[methylenebis(oxy)]bis Structure

2568-90-3

Butane,1,1'-[me...

1-(Dibutoxymethoxy)butane Structure

588-43-2

1-(Dibutoxymeth...

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Butyl nitrite Structure

544-16-1

Butyl nitrite

4-methoxy-N,N-dimethylaniline Structure

701-56-4

4-methoxy-N,N-d...

~38%

N-(4-methoxyphenyl)-N-methylnitrous amide Structure

940-11-4

N-(4-methoxyphe...

4-methoxy-N,N-dimethyl-2-nitroaniline Structure

60049-83-4

4-methoxy-N,N-d...

Detail Learn More
4-Bromo-N,N-dimethylaniline Structure

586-77-6

4-Bromo-N,N-dim...

~0%

Butane,1,1'-[methylenebis(oxy)]bis Structure

2568-90-3

Butane,1,1'-[me...

N-(4-bromophenyl)-N-methylnitrous amide Structure

937-23-5

N-(4-bromopheny...

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Butyl nitrite Structure

544-16-1

Butyl nitrite

4-Bromo-N,N-dimethylaniline Structure

586-77-6

4-Bromo-N,N-dim...

~0%

Butane,1,1'-[methylenebis(oxy)]bis Structure

2568-90-3

Butane,1,1'-[me...

N-(4-bromophenyl)-N-methylnitrous amide Structure

937-23-5

N-(4-bromopheny...

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