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Tele vs. Oxidative Substitution of Hydrogen in meta Monochloromethyl, Dichloromethyl, and Trichloromethyl Nitrobenzenes in the Reaction with Grignard Reagents

2003; Wiley; Volume: 2003; Issue: 19 Linguagem: Inglês

10.1002/ejoc.200300223

1434-193X

Mieczysław Mąkosza, George Varvounis, Marek Surowiec, Thomas Giannopoulo,

Chemical Reactions and Isotopes

Abstract Grignard reagents add to nitrobenzene derivatives containing trichloromethyl, dichloromethyl, and monochloromethyl groups in the meta position to form σ H adducts, which are either further converted through departure of a chloride anion, giving products of tele substitution, or oxidized to products of oxidative nucleophilic substitution of hydrogen. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)