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

Synthesis

High-pressure synthesis of oligoanilines

CL Brown, IW Muderawan, DJ Young

Index: Brown, Christopher L.; Muderawan, I. Wayan; Young, David J. Synthesis, 2003 , # 16 p. 2511 - 2517

Full Text: HTML

Citation Number: 4

Abstract

Branched oligoarylamines have been prepared by repetitive S N Ar reaction of the highly reactive 1-fluoro-2,4-dinitrobenzene with anilines followed by reduction. [7] The synthesis of linear oligomers requires reaction of 1-fluoro-4-nitrobenzene, but this electrophile is insufficiently reactive under conventional conditions [8] with the displacement of fluoride proceeding in low yield (6-11%) for aromatic amines at pressures of up to 0.9 GPa. [9] The effect of pressure on rate is ...

1-N,4-N-bis(4-nitrophenyl)benzene-1,4-diamine Structure

1-N,4-N-bis(4-n...

~%

1-N,4-N-bis[4-(2-nitroanilino)phenyl]benzene-1,4-diamine Structure

1-N,4-N-bis[4-(...

1-Fluoro-4-nitrobenzene Structure

1-Fluoro-4-nitr...

~%

1-N,4-N-bis[4-(2-nitroanilino)phenyl]benzene-1,4-diamine Structure

1-N,4-N-bis[4-(...

p-Phenylenediamine Structure

p-Phenylenediamine

~%

1-N,4-N-bis[4-(2-nitroanilino)phenyl]benzene-1,4-diamine Structure

1-N,4-N-bis[4-(...

N'',N'''-bis(2''-nitrophenyl)-N,N'-bis(4'-aminophenyl)-1,4-quinonediimine Structure

N'',N'''-bis(2'...

~81%

1-N,4-N-bis[4-(2-nitroanilino)phenyl]benzene-1,4-diamine Structure

1-N,4-N-bis[4-(...

N,N'-bis(4-aminophenyl)-1,4-benzoquinonediimine Structure

N,N'-bis(4-amin...

~%

1-N,4-N-bis[4-(2-nitroanilino)phenyl]benzene-1,4-diamine Structure

1-N,4-N-bis[4-(...

4-N-[4-(4-aminoanilino)phenyl]benzene-1,4-diamine Structure

4-N-[4-(4-amino...

1-Fluoro-2,4-dinitrobenzene Structure

1-Fluoro-2,4-di...

~96%

1-N,4-N-bis[4-(2,4-dinitroanilino)phenyl]benzene-1,4-diamine Structure

1-N,4-N-bis[4-(...

1-N,4-N-bis(4-nitrophenyl)benzene-1,4-diamine Structure

1-N,4-N-bis(4-n...

~%

1-N,4-N-bis[4-(2,4-dinitroanilino)phenyl]benzene-1,4-diamine Structure

1-N,4-N-bis[4-(...

1-Fluoro-4-nitrobenzene Structure

1-Fluoro-4-nitr...

~%

1-N,4-N-bis[4-(2,4-dinitroanilino)phenyl]benzene-1,4-diamine Structure

1-N,4-N-bis[4-(...

p-Phenylenediamine Structure

p-Phenylenediamine

~%

1-N,4-N-bis[4-(2,4-dinitroanilino)phenyl]benzene-1,4-diamine Structure

1-N,4-N-bis[4-(...

N'',N'''-bis(2'',4''-dinitrophenyl)-N,N'-bis(4'-aminophenyl)-1,4-quinonediimine Structure

N'',N'''-bis(2'...

~82%

1-N,4-N-bis[4-(2,4-dinitroanilino)phenyl]benzene-1,4-diamine Structure

1-N,4-N-bis[4-(...

1-Fluoro-2,4-dinitrobenzene Structure

1-Fluoro-2,4-di...

~%

1-N,4-N-bis[4-(2,4-dinitroanilino)phenyl]benzene-1,4-diamine Structure

1-N,4-N-bis[4-(...

N,N'-bis(4-aminophenyl)-1,4-benzoquinonediimine Structure

N,N'-bis(4-amin...

~%

1-N,4-N-bis[4-(2,4-dinitroanilino)phenyl]benzene-1,4-diamine Structure

1-N,4-N-bis[4-(...

o-Phenylenediamine Structure

o-Phenylenediamine

1-Fluoro-4-nitrobenzene Structure

1-Fluoro-4-nitr...

~21%

1-N,2-N-bis(4-nitrophenyl)benzene-1,2-diamine Structure

1-N,2-N-bis(4-n...

1-Fluoro-4-nitrobenzene Structure

1-Fluoro-4-nitr...

p-Phenylenediamine Structure

p-Phenylenediamine

~98%

1-N,4-N-bis(4-nitrophenyl)benzene-1,4-diamine Structure

1-N,4-N-bis(4-n...

p-Anisidine Structure

1-Fluoro-4-nitrobenzene Structure

1-Fluoro-4-nitr...

~99%

N-(4-methoxyphenyl)-4-nitroaniline Structure

N-(4-methoxyphe...

1-Fluoro-4-nitrobenzene Structure

1-Fluoro-4-nitr...

3-Nitroaniline Structure

~33%

3-nitro-N-(4-nitrophenyl)aniline Structure

3-nitro-N-(4-ni...

4-N-[4-(4-aminoanilino)phenyl]benzene-1,4-diamine Structure

4-N-[4-(4-amino...

1-Fluoro-4-nitrobenzene Structure

1-Fluoro-4-nitr...

~92%

1-N,4-N-bis[4-(4-nitroanilino)phenyl]benzene-1,4-diamine Structure

1-N,4-N-bis[4-(...

N'',N'''-bis(4''-nitrophenyl)-N,N'-bis(4'-aminophenyl)-1,4-quinonediimine Structure

N'',N'''-bis(4'...

~81%

1-N,4-N-bis[4-(4-nitroanilino)phenyl]benzene-1,4-diamine Structure

1-N,4-N-bis[4-(...

N,N'-bis(4-aminophenyl)-1,4-benzoquinonediimine Structure

N,N'-bis(4-amin...

~%

1-N,4-N-bis[4-(4-nitroanilino)phenyl]benzene-1,4-diamine Structure

1-N,4-N-bis[4-(...

1-N,4-N-bis(4-nitrophenyl)benzene-1,4-diamine Structure

1-N,4-N-bis(4-n...

~87%

4-N-[4-(4-aminoanilino)phenyl]benzene-1,4-diamine Structure

4-N-[4-(4-amino...