Reactions of organic anions. 174. Vicarious Nucleophilic Substitution of hydrogen (VNS) in nitrobenzofuroxans and the Boulton–Katritzky rearrangement of the VNS products

The Vicarious Nucleophilic Substitution of hydrogen in 4-nitrobenzofuroxan derivatives by carbanions of chloromethyl phenyl sulfone, chloromethyl p-tolyl sulfone, chloromethyl tert-butyl sulfone, and N,N-dimethyl chloromethane sulfonamide proceeds at positions 5 and 7. In some cases the Boulton–Katritzky rearrangement of the products obtained, leading to more stable 7-substituted isomers, was observed. Keywords: carbanions, nitrobenzofuroxans, sulfones, Vicarious Nucleophilic Substitution, Boulton–Katritzky rearrangement.