Simple Synthesis of Aryl p-Nitroarylacetonitriles via Vicarious Nucleophilic Substitution with Carbanions of Protected Cyanohydrins

Acetals of cyanohydrins of aromatic aldehydes upon deprotonation enter vicarious nucleophilic substitution of hydrogen with a series of carbo- and heteronitroarenes to form para-nitrosubstituted diarylacetonitriles. The reaction proceeds selectively in positions para to the nitro group. It was shown that anion of acetaldehyde hemiacetal is an efficient leaving group in base induced β-elimination.

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