Vicarious nucleophilic substitution

Vicarious nucleophilic substitution in organic chemistry is a special type of nucleophilic aromatic substitution in which a nucleophile replaces hydrogen and not an aromatic substituent like a halogen that is ordinarily encountered in this reaction type. This reaction type was introduce in 1987 by Mieczyslaw Makosza and Jerzy Winiarski.^[1]^[2]

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It is typically encountered with nitroarenes and especially with carbon nucleophiles, resulting in new alkylated arenes. Carbon nucleophiles carry a electron-withdrawing group and a nucleofuge:

References

^ Vicarious nucleophilic substitution of hydrogen. Mieczyslaw Makosza and Jerzy Winiarski. Acc. Chem. Res.; 1987; 20(8) pp 282 - 289; doi:10.1021/ar00140a003
^ Synthesis of heterocyclic compounds via vicarious nucleophilic substitution of hydrogen Mieczyslaw Mqkosza Pure & Appl. Chem., Vol. 69, No. 3, pp. 559-564, 1997 Article link.

Category: Organic reactions