Mononitrobenzene derivatives and 1-chloro-1-arylsulfonyl-methyl anions react with formation of stable σH adducts (see scheme; Ts=tosyl) which are observed by UV/Vis and NMR spectroscopy. The generally accepted energy profiles for vicarious nucleophilic substitutions with σH adducts as high-energy intermediates have to be revised.
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Lemek et al. (2003) studied this question.
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