Multiple Reaction Pathways between the Carbanions of α‐Alkoxy‐α‐phenylacetonitrile and o ‐Chloronitrobenzene

Carbanions of α‐methoxy‐ and α‐phenoxy‐α‐phenylacetonitriles undergo a variety of reactions with o ‐chloronitrobenzene by initial formation of σ H adducts and slower formation of σ Cl adducts. Reversible formation of σ H adducts followed by their fast transformation results in the formation of four different products with high selectivity. Slower addition in a position occupied by a chlorine atom to form σ Cl adducts results in a conventional S N Ar reaction. These five reaction pathways are efficiently controlled by the conditions and additional reagents.