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Reactions of Nucleophiles with Nitroarenes: Multifacial and Versatile Electrophiles
Authors:Prof. Dr. Mieczysław Mąkosza
Affiliation:Institute of Organic Chemistry, Polish Academy of Sciences ul. Kasprzaka 44/52, PO Box 58, 01‐224 Warszawa 42 (Poland), Fax: (+48)?22‐632‐66‐81
Abstract:In this overview, it is shown that there are many initial reactions between nitroarenes and nucleophiles: addition to the electron‐deficient ring at positions occupied by halogen and hydrogen atoms, addition to the nitro group, single‐electron transfer (SET), and other types of initial reactions. The resulting intermediates react further in a variety of ways to form products of nucleophilic substitution of a halogen atom (SNAr), a hydrogen atom (SNArH), and others. Many variants of these processes are briefly discussed, particularly in relation of rates of the initial reactions and further transformations.
Keywords:carbanions  nitroarenes  oxidation  single‐electron transfer  vicarious nucleophilic substitution
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