Abstract
AbstractStabilized carbanions of malonates, 2‐phenylacetonitrile, or isopropyl 2‐phenylacetate add to m‐(trichloromethyl)nitrobenzene derivatives to form σH adducts that lose a chloride ion to give intermediate exo‐dichloromethylene nitrocyclohexadienes. These undergo re‐aromatization through 1,5‐hydrogen shift to yield tele substitution mono adducts. Depending on the stoichiometry of the nitroarene to the carbanion, further addition of the nucleophile to the tele mono adduct can yield a mixture of products that are either double or triple adducts. At low temperature, the σH adducts undergo direct 1,2‐addition in competition with chloride ion elimination/1,5‐hydrogen shift.
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