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

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 ...

N,N-Dimethylaniline Structure

N,N-Dimethylaniline

~4%

n-nitroso-n-methylaniline Structure

n-nitroso-n-met...

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

N,N-Dimethyl-4-...

N/A Structure

Detail

N,N-Dimethylaniline Structure

N,N-Dimethylaniline

~30%

N-methyl-N,4-dinitrosoaniline Structure

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

n-nitroso-n-methylaniline Structure

n-nitroso-n-met...

4-Bromo-N,N-dimethylaniline Structure

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

~89%

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

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

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

N-(4-bromopheny...

Butyl nitrite Structure

4-Bromo-N,N-dimethylaniline Structure

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

~88%

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

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

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

N-(4-bromopheny...

4-Bromo-N,N-dimethylaniline Structure

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

~58%

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

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

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

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

N,N-DIMETHYL-4-NITROANILINE Structure

N,N-DIMETHYL-4-...

Detail

Butyl nitrite Structure

4-Bromo-N,N-dimethylaniline Structure

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

~78%

Formaldehyde Structure

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

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

Detail

Butyl nitrite Structure

4-Bromo-N,N-dimethylaniline Structure

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

~20%

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

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

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

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

Detail

Butyl nitrite Structure

4-Bromo-N,N-dimethylaniline Structure

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

~0%

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

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

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

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

Detail

4-methoxy-N,N-dimethylaniline Structure

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

~81%

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

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

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

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

N/A Structure

Butyl nitrite Structure

4-methoxy-N,N-dimethylaniline Structure

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

~86%

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

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

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

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

Detail

Butyl nitrite Structure

4-methoxy-N,N-dimethylaniline Structure

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

~29%

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

N-(4-methoxyphe...

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

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

Detail

4-Bromo-N,N-dimethylaniline Structure

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

~6%

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

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

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

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

N,N-DIMETHYL-4-NITROANILINE Structure

N,N-DIMETHYL-4-...

Detail

Butyl nitrite Structure

4-Bromo-N,N-dimethylaniline Structure

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

~0%

Formaldehyde Structure

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

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

Detail

N,N-Dimethylaniline Structure

N,N-Dimethylaniline

~0%

N-methyl-N,4-dinitrosoaniline Structure

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

n-nitroso-n-methylaniline Structure

n-nitroso-n-met...

Butyl nitrite Structure

4-methoxy-N,N-dimethylaniline Structure

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

~66%

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

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

1-(Dibutoxymethoxy)butane Structure

1-(Dibutoxymeth...

Detail

Butyl nitrite Structure

4-methoxy-N,N-dimethylaniline Structure

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

~38%

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

N-(4-methoxyphe...

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

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

Detail

4-Bromo-N,N-dimethylaniline Structure

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

~0%

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

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

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

N-(4-bromopheny...

Butyl nitrite Structure

4-Bromo-N,N-dimethylaniline Structure

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

~0%

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

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

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

N-(4-bromopheny...

Amine-induced reactions of diacyl peroxides

[Srinivas, Shamala; Taylor, K. Grant Journal of Organic Chemistry, 1990 , vol. 55, # 6 p. 1779 - 1786]

Photochemical reaction of diaryliodomium salts with dimethyl...

[Bi, Yubai; Neckers, Douglas C. Tetrahedron Letters, 1992 , vol. 33, # 9 p. 1139 - 1142]

Amine-induced reactions of diacyl peroxides

[Srinivas, Shamala; Taylor, K. Grant Journal of Organic Chemistry, 1990 , vol. 55, # 6 p. 1779 - 1786]