Chlorination features of 1,5-dinitro-3-azabicyclo[3.3.1]non-6-enes

The electrophilic chlorine addition to 3-substituted 1,5-dinitro-3-azabicyclo[3.3.1]-non-6-enes in the tetrachloromethane is accompanied at an intramolecular 3,7-cyclization giving 6-chloro-3-R-1,5-dinitro-3-azoniatricyclo[3.3.1.03,7]nonane chlorides. The reaction of the tricyclic quaternary ammonium salts with sodium methoxide leads to the formation of dealkylated and dehydrohalogenated products, 3-substituted 8-chloro-1,5-dinitro-3-azabicyclo[3.3.1]non-6-enes, bicyclic products with a halogen atom in an allyl position with respect to the double bond.