Condensation-Cyclization of Acetoacetanilides with 1,3,5-Trinitrobenzene. Formation and Structure of Some Stable Delocalized Anions Containing the Bicyclononane Skeleton

Article abstract of DOI:10.1021/jo00152a031

A series of new bicyclic anions containing the bicyclo<3.3.1>nonane skeleton have been prepared from 1,3,5-trinitrobenzene and carbanions derived from substituted acetoacetanilides.The condensation-cyclizations are initiated by triethylamine.A mechanistic picture for the cyclization is shown as proceeding through a delocalized carbanion intermediate.