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

Alkyl nitrite-metal halide deamination reactions. 7. Synthetic coupling of electrophilic bromination with substitutive deamination for selective synthesis of multiply …

…, MA Van Lente, R Mowat, WF Fobare

Index: Doyle, Michael P.; Lente, Michael A. van; Mowat, Rex; Fobare, William F. Journal of Organic Chemistry, 1980 , vol. 45, # 13 p. 2570 - 2575

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Citation Number: 32

Abstract

Aromatic amines undergo oxidative substitution with copper (I1) bromide that is in competition with substitutive deamination when these reactions are performed with tert-butyl nitrite. Except for the exceptionally reactive 4-substituted 1-aminonaphthalenes, which undergo selective bromine substitution at the 1-and 2-positions in relatively high isolated yields, rates for oxidative bromination and substitutive deamination are not sufficiently ...

4-Nitroaniline Structure

~96%

1,2,3-Tribromo-5-nitrobenzene Structure

1,2,3-Tribromo-...

4-Nitroaniline Structure

~%

1,2-dibromo-4-nitro-benzene Structure

1,2-dibromo-4-n...

1,2,3-Tribromo-5-nitrobenzene Structure

1,2,3-Tribromo-...

1-Bromo-4-nitrobenzene Structure

1-Bromo-4-nitro...

4-Chloroaniline Structure

4-Chloroaniline

~85%

1-CHLORO-3,4,5-TRIBROMOBENZENE Structure

1-CHLORO-3,4,5-...

4-Chloroaniline Structure

4-Chloroaniline

~%

4-Bromochlorobenzene Structure

4-Bromochlorobenzene

3,4-Dibromochlorobenzene Structure

3,4-Dibromochlo...

1-CHLORO-3,4,5-TRIBROMOBENZENE Structure

1-CHLORO-3,4,5-...

N,N-Dimethylaniline Structure

N,N-Dimethylaniline

~10%

4-Bromo-N,N-dimethylaniline Structure

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

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

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

2,4-dibromo-N-methylaniline Structure

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

N,N-Dimethylaniline Structure

N,N-Dimethylaniline

~5%

4-Bromo-N,N-dimethylaniline Structure

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

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

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

2,4-dibromo-N-methylaniline Structure

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

Detail

N,N-Dimethylaniline Structure

N,N-Dimethylaniline

~5%

4-Bromo-N,N-dimethylaniline Structure

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

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

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

2,4-dibromo-N-methylaniline Structure

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

N,N-Dimethylaniline Structure

N,N-Dimethylaniline

~16%

4-Bromo-N,N-dimethylaniline Structure

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

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

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

2,4-dibromo-N-methylaniline Structure

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

Detail

2,5-Dichloroaniline Structure

2,5-Dichloroaniline

~2%

Benzene,1,4-dibromo-2,5-dichloro- Structure

Benzene,1,4-dib...

1,3,4-Tribromo-2,5-dichlorobenzene Structure

1,3,4-Tribromo-...

4-Bromoaniline Structure

~99%

1,2,3,5-tetrabromobenzene Structure

1,2,3,5-tetrabr...

p-Toluidine Structure

~98%

3,4,5-TRIBROMOTOLUENE Structure

3,4,5-TRIBROMOT...

p-Toluidine Structure

~%

4-Bromotoluene Structure

1,2-Dibromo-4-methylbenzene Structure

1,2-Dibromo-4-m...

3,4,5-TRIBROMOTOLUENE Structure

3,4,5-TRIBROMOT...

1-Naphthalenamine,4-chloro- Structure

1-Naphthalenami...

~%

1-Bromo-4-chloronaphthalene Structure

1-Bromo-4-chlor...

1,2-dibromo-4-chloronaphthalene Structure

1,2-dibromo-4-c...

4-Nitro-1-naphthalenamine Structure

4-Nitro-1-napht...

~%

1-Bromo-4-nitronaphthalene Structure

1-Bromo-4-nitro...

1,2-dibromo-4-nitronaphthalene Structure

1,2-dibromo-4-n...

3,4-Dichloroaniline Structure

3,4-Dichloroaniline

~4%

1,2,3-tribromo-4,5-dichlorobenzene Structure

1,2,3-tribromo-...

1,2-dibromo-4,5-dichlorobenzene Structure

1,2-dibromo-4,5...

1-Aryl-3, 3-dialkyltriazenes: A convenient synthesis from dr...

[Barbero; Degani; Diulgheroff; Dughera; Fochi Synthesis, 2001 , # 14 p. 2180 - 2190]