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Evaluation of Electrophilic Activities of Substituted Nitroarenes in the VNS Reaction with Secondary and Tertiary Carbanions

Błażej S., Wileńska B., Voynova N. S., Mąkosza M.

Polish Journal of Chemistry

2008

Vol. 82, nr 10

2017-2030

Relative electrophilic activities of substituted nitroarenes in the vicarious nucleophilic substitution (VNS) reaction with carbanion of chloromethyl p-chlorophenyl and bromo - methyl phenyl sulfones, 1 and 2, were determined via competitive experiments. The results are in good agreement with relative activities determined earlier in the competitive experiments with carbanion of chloromethyl phenyl sulfone 3 confirming reliability of these data. On the other hand, analogous competitive experiments with tertiary carbanions of chloroform and 1-chloroethyl phenyl sulfone gave results much affected by steric effects thus the VNS reaction with these carbanions can not be used for evaluation of electrophilic activities of nitroarenes.

Oxidative Nucleophilic Substitution of Hydrogen in nitroarenes. A Short Review

Mąkosza M., Paszewski M.

Polish Journal of Chemistry

2005

Vol. 79 / nr 2

163-178

Recent results of oxidative nucleophilic substitution of hydrogen in nitroarenes with carbon, nitrogen, oxygen etc. nucleophiles and discussion of oxidants used in these reactions are presented.

Influence of conjugation on orientation in substituted nitropyridines: Vicarious Nucleophilic Substitution of Hydrogen with chloromethyl phenyl sulfone

Mąkosza M., Ludwiczak S.

Polish Journal of Chemistry

1998

Vol. 72, nr 7

1168-1172

2-Hydroxy- and 2-mercapto-5-nitropyridines as well as their O- ( and S-) substituted derivatives enter Vicarious Nucleophilic Substitution of Hydrogen (VNS) with chloromethyl phenyl sulfone. The orientation of the substitution can be controlled by varying the O- (or S-) substituent. The results of VNS in 4-methoxy-3-nitropyridine and 3-methoxy-2-nitropyridine are also reported.

Ambiphilic reactivity of 2,4-dinitrobenzyl p-tolyl sulfone carbanion

Mąkosza M., Mathur S.N., Białecki M.

Polish Journal of Chemistry

1998

Vol. 72, nr 7

1198-1201

Carbanions of 2,4-dinitrobenzyl p-tolyl sulfone (3a) and 5-chloro-2,4-dinitrobenzyl p-tolyl sulfone (3b) behave as ambiphilic reagents able to react with nucleophiles and electrophiles. The reaction course depends on the type of the reagent and of the base used in the reaction.