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

Chemistry–A European Journal

Substituent Effects on the Electrophilic Activity of Nitroarenes in Reactions with Carbanions

S Błażej, M Mąkosza

Index: Blazej, Sylwia; Makosza, Mieczyslaw Chemistry - A European Journal, 2008 , vol. 14, # 35 p. 11113 - 11122

Full Text: HTML

Citation Number: 17

Abstract

Abstract The effect on electrophilic activity of substituents located para, ortho, and meta to the nitro group of nitrobenzenes was determined by using vicarious nucleophilic substitution of hydrogen (VNS) with the carbanion of chloromethyl phenyl sulfone (1) as the model process. Values for the relative activities of substituted nitroarenes are given relative to nitrobenzene, which was taken as the standard. This process was chosen as a model ...

3-Nitrotoluene Structure

CHLOROMETHYL PHENYL SULFONE Structure

CHLOROMETHYL PH...

Benzene,1-(1,1-dimethylethyl)-4-nitro- Structure

Benzene,1-(1,1-...

~%

1-(benzenesulfonylmethyl)-4-methyl-2-nitrobenzene Structure

1-(benzenesulfo...

Detail

CHLOROMETHYL PHENYL SULFONE Structure

CHLOROMETHYL PH...

4-NITROPHENYL PHENYL ETHER Structure

4-NITROPHENYL P...

nitrobenzene Structure

~%

1-(benzenesulfonylmethyl)-2-nitrobenzene Structure

1-(benzenesulfo...

Detail

m-nitroanisole Structure

CHLOROMETHYL PHENYL SULFONE Structure

CHLOROMETHYL PH...

4-NITROPHENYL PHENYL ETHER Structure

4-NITROPHENYL P...

~%

1-(benzenesulfonylmethyl)-4-methoxy-2-nitrobenzene Structure

1-(benzenesulfo...

Detail

3-Nitrochlorobenzene Structure

3-Nitrochlorobenzene

CHLOROMETHYL PHENYL SULFONE Structure

CHLOROMETHYL PH...

~97%

1-(benzenesulfonylmethyl)-2-chloro-4-nitrobenzene Structure

1-(benzenesulfo...

3-Bromonitrobenzene Structure

3-Bromonitrobenzene

CHLOROMETHYL PHENYL SULFONE Structure

CHLOROMETHYL PH...

4-Chloronitrobenzene Structure

4-Chloronitrobenzene

~%

1-(benzenesulfonylmethyl)-4-bromo-2-nitrobenzene Structure

1-(benzenesulfo...

Detail

m-nitroanisole Structure

CHLOROMETHYL PHENYL SULFONE Structure

CHLOROMETHYL PH...

4-NITROPHENYL PHENYL ETHER Structure

4-NITROPHENYL P...

~%

1-(benzenesulfonylmethyl)-4-methoxy-2-nitrobenzene Structure

1-(benzenesulfo...

Detail

3-Fluoronitrobenzene Structure

3-Fluoronitrobenzene

CHLOROMETHYL PHENYL SULFONE Structure

CHLOROMETHYL PH...

4-Chloronitrobenzene Structure

4-Chloronitrobenzene

~%

1-(benzenesulfonylmethyl)-4-fluoro-2-nitrobenzene Structure

1-(benzenesulfo...

Detail

CHLOROMETHYL PHENYL SULFONE Structure

CHLOROMETHYL PH...

nitrobenzene Structure

2-Nitrochlorobenzene Structure

2-Nitrochlorobenzene

~%

1-(benzenesulfonylmethyl)-2-nitrobenzene Structure

1-(benzenesulfo...

Detail

CHLOROMETHYL PHENYL SULFONE Structure

CHLOROMETHYL PH...

4-Chloronitrobenzene Structure

4-Chloronitrobenzene

2-Nitrochlorobenzene Structure

2-Nitrochlorobenzene

~%

2-(benzenesulfonylmethyl)-4-chloro-1-nitrobenzene Structure

2-(benzenesulfo...

Detail

CHLOROMETHYL PHENYL SULFONE Structure

CHLOROMETHYL PH...

Benzene,1-(1,1-dimethylethyl)-4-nitro- Structure

Benzene,1-(1,1-...

nitrobenzene Structure

~%

1-(benzenesulfonylmethyl)-2-nitrobenzene Structure

1-(benzenesulfo...

Detail

3-Nitrotoluene Structure

CHLOROMETHYL PHENYL SULFONE Structure

CHLOROMETHYL PH...

Benzene,1-(1,1-dimethylethyl)-4-nitro- Structure

Benzene,1-(1,1-...

~%

1-(benzenesulfonylmethyl)-4-methyl-2-nitrobenzene Structure

1-(benzenesulfo...

Detail

CHLOROMETHYL PHENYL SULFONE Structure

CHLOROMETHYL PH...

1-Nitro-2-(trifluoromethyl)benzene Structure

1-Nitro-2-(trif...

4-Chloronitrobenzene Structure

4-Chloronitrobenzene

~%

2-(benzenesulfonylmethyl)-4-chloro-1-nitrobenzene Structure

2-(benzenesulfo...

Detail

3-Nitrotoluene Structure

CHLOROMETHYL PHENYL SULFONE Structure

CHLOROMETHYL PH...

Benzene,1-(1,1-dimethylethyl)-4-nitro- Structure

Benzene,1-(1,1-...

~%

1-(benzenesulfonylmethyl)-4-methyl-2-nitrobenzene Structure

1-(benzenesulfo...

Detail

m-nitroanisole Structure

CHLOROMETHYL PHENYL SULFONE Structure

CHLOROMETHYL PH...

4-NITROPHENYL PHENYL ETHER Structure

4-NITROPHENYL P...

~%

1-(benzenesulfonylmethyl)-4-methoxy-2-nitrobenzene Structure

1-(benzenesulfo...

Detail

1-Iodo-4-nitrobenzene Structure

1-Iodo-4-nitrob...

CHLOROMETHYL PHENYL SULFONE Structure

CHLOROMETHYL PH...

4-Chloronitrobenzene Structure

4-Chloronitrobenzene

~%

2-(benzenesulfonylmethyl)-4-chloro-1-nitrobenzene Structure

2-(benzenesulfo...

Detail

CHLOROMETHYL PHENYL SULFONE Structure

CHLOROMETHYL PH...

Benzene,1-(1,1-dimethylethyl)-4-nitro- Structure

Benzene,1-(1,1-...

nitrobenzene Structure

~%

1-(benzenesulfonylmethyl)-2-nitrobenzene Structure

1-(benzenesulfo...

Detail

CHLOROMETHYL PHENYL SULFONE Structure

CHLOROMETHYL PH...

4-NITROPHENYL PHENYL ETHER Structure

4-NITROPHENYL P...

nitrobenzene Structure

~%

1-(benzenesulfonylmethyl)-2-nitrobenzene Structure

1-(benzenesulfo...

Detail

CHLOROMETHYL PHENYL SULFONE Structure

CHLOROMETHYL PH...

nitrobenzene Structure

4-Chloronitrobenzene Structure

4-Chloronitrobenzene

~%

1-(benzenesulfonylmethyl)-2-nitrobenzene Structure

1-(benzenesulfo...

Detail

CHLOROMETHYL PHENYL SULFONE Structure

CHLOROMETHYL PH...

nitrobenzene Structure

2-Nitrochlorobenzene Structure

2-Nitrochlorobenzene

~%

1-(benzenesulfonylmethyl)-2-nitrobenzene Structure

1-(benzenesulfo...

Detail

3-Fluoronitrobenzene Structure

3-Fluoronitrobenzene

CHLOROMETHYL PHENYL SULFONE Structure

CHLOROMETHYL PH...

4-Chloronitrobenzene Structure

4-Chloronitrobenzene

~%

1-(benzenesulfonylmethyl)-4-fluoro-2-nitrobenzene Structure

1-(benzenesulfo...

Detail

CHLOROMETHYL PHENYL SULFONE Structure

CHLOROMETHYL PH...

2-Chloro-1-nitro-4-(trifluoromethyl)benzene Structure

2-Chloro-1-nitr...

3-Nitrobenzonitrile Structure

3-Nitrobenzonitrile

~%

3-chloro-2-nitro-5-trifluoromethylbenzyl phenyl sulfone Structure

3-chloro-2-nitr...

Detail

CHLOROMETHYL PHENYL SULFONE Structure

CHLOROMETHYL PH...

4-Chloronitrobenzene Structure

4-Chloronitrobenzene

1-Bromo-4-nitrobenzene Structure

1-Bromo-4-nitro...

~%

2-(benzenesulfonylmethyl)-4-bromo-1-nitrobenzene Structure

2-(benzenesulfo...

Detail

3-Nitrotoluene Structure

CHLOROMETHYL PHENYL SULFONE Structure

CHLOROMETHYL PH...

Benzene,1-(1,1-dimethylethyl)-4-nitro- Structure

Benzene,1-(1,1-...

~%

1-(benzenesulfonylmethyl)-4-methyl-2-nitrobenzene Structure

1-(benzenesulfo...

Detail

m-nitroanisole Structure

CHLOROMETHYL PHENYL SULFONE Structure

CHLOROMETHYL PH...

4-NITROPHENYL PHENYL ETHER Structure

4-NITROPHENYL P...

~%

1-(benzenesulfonylmethyl)-4-methoxy-2-nitrobenzene Structure

1-(benzenesulfo...

Detail

CHLOROMETHYL PHENYL SULFONE Structure

CHLOROMETHYL PH...

4-Chloronitrobenzene Structure

4-Chloronitrobenzene

4-Nitrobenzonitrile Structure

4-Nitrobenzonitrile

~%

2-(benzenesulfonylmethyl)-4-chloro-1-nitrobenzene Structure

2-(benzenesulfo...

Detail

1-Nitronaphthalene Structure

1-Nitronaphthalene

4-Nitrobenzotrifluoride Structure

4-Nitrobenzotri...

CHLOROMETHYL PHENYL SULFONE Structure

CHLOROMETHYL PH...

~%

(1-nitro-2-naphthyl)methyl phenyl sulfone Structure

(1-nitro-2-naph...

Detail

1-Iodo-3-nitrobenzene Structure

1-Iodo-3-nitrob...

CHLOROMETHYL PHENYL SULFONE Structure

CHLOROMETHYL PH...

4-Chloronitrobenzene Structure

4-Chloronitrobenzene

~%

1-(benzenesulfonylmethyl)-4-iodo-2-nitrobenzene Structure

1-(benzenesulfo...

Detail

3-Fluoronitrobenzene Structure

3-Fluoronitrobenzene

CHLOROMETHYL PHENYL SULFONE Structure

CHLOROMETHYL PH...

4-Chloronitrobenzene Structure

4-Chloronitrobenzene

~%

1-(benzenesulfonylmethyl)-4-fluoro-2-nitrobenzene Structure

1-(benzenesulfo...

Detail

3-Nitrochlorobenzene Structure

3-Nitrochlorobenzene

CHLOROMETHYL PHENYL SULFONE Structure

CHLOROMETHYL PH...

4-Chloronitrobenzene Structure

4-Chloronitrobenzene

~%

1-(benzenesulfonylmethyl)-4-chloro-2-nitrobenzene Structure

1-(benzenesulfo...

Detail

3-Nitrochlorobenzene Structure

3-Nitrochlorobenzene

CHLOROMETHYL PHENYL SULFONE Structure

CHLOROMETHYL PH...

~%

1-(benzenesulfonylmethyl)-4-chloro-2-nitrobenzene Structure

1-(benzenesulfo...

2-(benzenesulfonylmethyl)-1-chloro-3-nitrobenzene Structure

2-(benzenesulfo...

3-Bromonitrobenzene Structure

3-Bromonitrobenzene

CHLOROMETHYL PHENYL SULFONE Structure

CHLOROMETHYL PH...

4-Chloronitrobenzene Structure

4-Chloronitrobenzene

~%

1-(benzenesulfonylmethyl)-4-bromo-2-nitrobenzene Structure

1-(benzenesulfo...

Detail

CHLOROMETHYL PHENYL SULFONE Structure

CHLOROMETHYL PH...

2-Chloro-1-nitro-4-(trifluoromethyl)benzene Structure

2-Chloro-1-nitr...

3-Nitrobenzonitrile Structure

3-Nitrobenzonitrile

~%

3-chloro-2-nitro-5-trifluoromethylbenzyl phenyl sulfone Structure

3-chloro-2-nitr...

Detail

CHLOROMETHYL PHENYL SULFONE Structure

CHLOROMETHYL PH...

nitrobenzene Structure

2-Nitrochlorobenzene Structure

2-Nitrochlorobenzene

~%

1-(benzenesulfonylmethyl)-2-nitrobenzene Structure

1-(benzenesulfo...

Detail

CHLOROMETHYL PHENYL SULFONE Structure

CHLOROMETHYL PH...

4-Chloronitrobenzene Structure

4-Chloronitrobenzene

2-Nitrochlorobenzene Structure

2-Nitrochlorobenzene

~%

2-(benzenesulfonylmethyl)-4-chloro-1-nitrobenzene Structure

2-(benzenesulfo...

Detail

1-Iodo-4-nitrobenzene Structure

1-Iodo-4-nitrob...

CHLOROMETHYL PHENYL SULFONE Structure

CHLOROMETHYL PH...

4-Chloronitrobenzene Structure

4-Chloronitrobenzene

~%

2-(benzenesulfonylmethyl)-4-chloro-1-nitrobenzene Structure

2-(benzenesulfo...

Detail

Benzoicacid, 4-nitro-, 1-methylethyl ester Structure

Benzoicacid, 4-...

CHLOROMETHYL PHENYL SULFONE Structure

CHLOROMETHYL PH...

4-Chloronitrobenzene Structure

4-Chloronitrobenzene

~%

isopropyl 4-nitro-3-((phenylsulfonyl)methyl)benzoate Structure

isopropyl 4-nit...

Detail

(4-Nitrophenyl)(phenyl)sulfane Structure

(4-Nitrophenyl)...

CHLOROMETHYL PHENYL SULFONE Structure

CHLOROMETHYL PH...

4-Chloronitrobenzene Structure

4-Chloronitrobenzene

~%

2-nitro-5-phenylthiobenzyl phenyl sulfone Structure

2-nitro-5-pheny...

Detail

CHLOROMETHYL PHENYL SULFONE Structure

CHLOROMETHYL PH...

nitrobenzene Structure

4-Chloronitrobenzene Structure

4-Chloronitrobenzene

~%

1-(benzenesulfonylmethyl)-2-nitrobenzene Structure

1-(benzenesulfo...

Detail

CHLOROMETHYL PHENYL SULFONE Structure

CHLOROMETHYL PH...

4-Chloronitrobenzene Structure

4-Chloronitrobenzene

1-Bromo-4-nitrobenzene Structure

1-Bromo-4-nitro...

~%

2-(benzenesulfonylmethyl)-4-bromo-1-nitrobenzene Structure

2-(benzenesulfo...

Detail

CHLOROMETHYL PHENYL SULFONE Structure

CHLOROMETHYL PH...

4-Chloronitrobenzene Structure

4-Chloronitrobenzene

4-Nitrobenzonitrile Structure

4-Nitrobenzonitrile

~%

2-(benzenesulfonylmethyl)-4-chloro-1-nitrobenzene Structure

2-(benzenesulfo...

Detail

1-Iodo-3-nitrobenzene Structure

1-Iodo-3-nitrob...

CHLOROMETHYL PHENYL SULFONE Structure

CHLOROMETHYL PH...

4-Chloronitrobenzene Structure

4-Chloronitrobenzene

~%

1-(benzenesulfonylmethyl)-4-iodo-2-nitrobenzene Structure

1-(benzenesulfo...

Detail

3-Nitrochlorobenzene Structure

3-Nitrochlorobenzene

CHLOROMETHYL PHENYL SULFONE Structure

CHLOROMETHYL PH...

4-Chloronitrobenzene Structure

4-Chloronitrobenzene

~%

1-(benzenesulfonylmethyl)-4-chloro-2-nitrobenzene Structure

1-(benzenesulfo...

Detail

3-Bromonitrobenzene Structure

3-Bromonitrobenzene

CHLOROMETHYL PHENYL SULFONE Structure

CHLOROMETHYL PH...

4-Chloronitrobenzene Structure

4-Chloronitrobenzene

~%

1-(benzenesulfonylmethyl)-4-bromo-2-nitrobenzene Structure

1-(benzenesulfo...

Detail

CHLOROMETHYL PHENYL SULFONE Structure

CHLOROMETHYL PH...

1-Nitro-2-(trifluoromethyl)benzene Structure

1-Nitro-2-(trif...

4-Chloronitrobenzene Structure

4-Chloronitrobenzene

~%

2-(benzenesulfonylmethyl)-4-chloro-1-nitrobenzene Structure

2-(benzenesulfo...

Detail

CHLOROMETHYL PHENYL SULFONE Structure

CHLOROMETHYL PH...

i-propyl 2-nitrobenzoate Structure

i-propyl 2-nitr...

4-Chloronitrobenzene Structure

4-Chloronitrobenzene

~%

isopropyl 2-nitro-5-((phenylsulfonyl)methyl)benzoate Structure

isopropyl 2-nit...

Detail

CHLOROMETHYL PHENYL SULFONE Structure

CHLOROMETHYL PH...

Methyl 3-nitrobenzoate Structure

Methyl 3-nitrob...

4-Chloronitrobenzene Structure

4-Chloronitrobenzene

~%

2-(benzenesulfonylmethyl)-4-chloro-1-nitrobenzene Structure

2-(benzenesulfo...

Detail

CHLOROMETHYL PHENYL SULFONE Structure

CHLOROMETHYL PH...

4-Chloronitrobenzene Structure

4-Chloronitrobenzene

2-Nitrochlorobenzene Structure

2-Nitrochlorobenzene

~%

2-(benzenesulfonylmethyl)-4-chloro-1-nitrobenzene Structure

2-(benzenesulfo...

Detail

CHLOROMETHYL PHENYL SULFONE Structure

CHLOROMETHYL PH...

4-Chloronitrobenzene Structure

4-Chloronitrobenzene

2-Nitrobenzonitrile Structure

2-Nitrobenzonitrile

~%

3-cyano-2-nitrobenzyl phenyl sulfone Structure

3-cyano-2-nitro...

Detail

3-Fluoronitrobenzene Structure

3-Fluoronitrobenzene

CHLOROMETHYL PHENYL SULFONE Structure

CHLOROMETHYL PH...

4-Chloronitrobenzene Structure

4-Chloronitrobenzene

~%

1-(benzenesulfonylmethyl)-4-fluoro-2-nitrobenzene Structure

1-(benzenesulfo...

Detail

CHLOROMETHYL PHENYL SULFONE Structure

CHLOROMETHYL PH...

1-Nitro-2-(trifluoromethyl)benzene Structure

1-Nitro-2-(trif...

4-Chloronitrobenzene Structure

4-Chloronitrobenzene

~%

2-(benzenesulfonylmethyl)-4-chloro-1-nitrobenzene Structure

2-(benzenesulfo...

Detail

3-Nitrochlorobenzene Structure

3-Nitrochlorobenzene

CHLOROMETHYL PHENYL SULFONE Structure

CHLOROMETHYL PH...

4-Chloronitrobenzene Structure

4-Chloronitrobenzene

~%

1-(benzenesulfonylmethyl)-4-chloro-2-nitrobenzene Structure

1-(benzenesulfo...

Detail

3-Nitrochlorobenzene Structure

3-Nitrochlorobenzene

CHLOROMETHYL PHENYL SULFONE Structure

CHLOROMETHYL PH...

~%

1-(benzenesulfonylmethyl)-4-chloro-2-nitrobenzene Structure

1-(benzenesulfo...

2-(benzenesulfonylmethyl)-1-chloro-3-nitrobenzene Structure

2-(benzenesulfo...

Specific ortho orientation in the vicarious substitution of ...

[Makosza, M.; Glinka, T.; Kinowski, A. Tetrahedron, 1984 , vol. 40, # 10 p. 1863 - 1868]

Reactions of organic anions. Part 109. Vicarious nucleophili...

[Makosza, Mieczyslaw; Golinski, Jerzy; Baran, Janusz Journal of Organic Chemistry, 1984 , vol. 49, # 9 p. 1488 - 1494]

Specific ortho orientation in the vicarious substitution of ...

[Makosza, M.; Glinka, T.; Kinowski, A. Tetrahedron, 1984 , vol. 40, # 10 p. 1863 - 1868]

Specific ortho orientation in the vicarious substitution of ...

[Makosza, M.; Glinka, T.; Kinowski, A. Tetrahedron, 1984 , vol. 40, # 10 p. 1863 - 1868]

Reactions of organic anions. Part 109. Vicarious nucleophili...

[Makosza, Mieczyslaw; Golinski, Jerzy; Baran, Janusz Journal of Organic Chemistry, 1984 , vol. 49, # 9 p. 1488 - 1494]