Reformatsky Reaction of Methyl 1-Bromocyclohexanecarboxylate with N,N′-(1,4-Phenylene)bis(1-arylmethanimines)

Abstract

Reformatsky reagent prepared from methyl 1-bromocyclohexanecarboxylate reacted with N,N′-(1,4-phenylene)bis(1-arylmethanimines) to produce 2,2′-(1,4-phenylene)bis[3-aryl-2-azaspiro[3.5]nonan-1-ones] as a result of successive nucleophilic additions to the C=N double bonds of the substrate and intramolecular cyclization of the corresponding intermediates. The stepwise reaction mechanism was proved by the isolation of 2-[4-(arylmethylideneamino)phenyl]-3-aryl-2-azaspiro[3.5]nonan-1-ones in the reactions with equimolar amounts of the Schiff base and Reformatsky reagent.