Synthesis and conversions of polyhedral compounds 19. Opening of ring of 1,3,6-triazohomoadamantane by electrophilic reagents

A new method has been developed for obtaining 8-nitro-1,3,6-triazahomoadamantane. By the action of electrophilic reagents on this compound, N-C bonds of the methylenediamino fragment are ruptured, forming derivatives of 1,4,8-triazabicyclo4.3.1]decane. Depending on the conditions in reactions of 8-nitro-1,3,6-triazohomoadamantane with benzoyl chloride and nitrous acid, derivatives of either 1,4,8-triazabicyclo4.3.1]decane or hexahydro-1,4-diazepine may be obtained. The formation of the latter proceeds through the above-mentioned derivatives of 1,4,8-triazabicyclo4.3.1]decane.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 397–400, March, 1994.