Abstract
3-Nitro-ω-benzylideneacetophenone (1) reacts with carbanions containing leaving groups to give addition products to the electrophilic side chain. As a result of conjugated addition and subsequent intramolecular vicarious nucleophilic substitution of hydrogen (VNS) in the nitroaromatic ring of 1 in the position para to the nitro group, 4-cyano-7-nitro-3-phenyl-1,2,3,4-tetrahydronaphthalen-1-one and 4-cyano-7-nitro-3-phenylnaphth-1-ol are obtained. Smooth intramolecular VNS in the position para to the nitro group was observed for 4-chloro-1-(3-nitrophenyl)-3-phenyl-4-(p-tosyl)butanol.
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