REACTIONS OF 3-NITRO-OMEGA-BENZYLIDENEACETOPHENONE WITH CARBANIONS CONTAINING LEAVING GROUPS

3-Nitro-omega-benzylideneacetophenone (1) reacts with carbanions conta ining leaving groups to give addition products to the electrophilic si de chain. As a result of conjugated addition and subsequent intramolec ular vicarious nutreophilic substitution of hydrogen (VNS) in the nitr oaromatic ring of 1 in the position para to the nitro group, -nitro-3- phenyl-1,2,3,4-tetrahydronaphthalen-1-one and 4-cyano-7-nitro-3-phenyl naphth-1-ol are obtained. Smooth intramolecular VNS in the position pa ra to the nitro group was observed for oro-1-(3-nitrophenyl)-3-phenyl- 4-(p-tosyl)butanol.