Diazabicycloalkanes with nitrogen atoms in the nodal positions. 8. Effect of c-substituents on the N-methylation of 1,4-diazabi cyclo[2.2.2]octanes and the demethylation of their bisquaternary salts

Article abstract of DOI:10.1007/BF00512969

The introduction of substituents with various inductive constants in the 2 position of the diazabicyclo]2.2.2]octane ring gives rise to a change in the pK_a values and affects the ease of introduction of a methyl group in the 1 and 4 positions, as well as the rate of demethylation of the bisquaternary salts from the 1 position. When 1,4-diazabicyclo[2.2.2]octane is treated with a sufficiently strong nucleophile, the ring is opened to give a piperazine derivative.