Addition of bromine to 2-methyl-2-azabicyclo[2.2.1]hept-5-ene was studied.
Unexpectedly, 3-bromo-1-methyl-1-azoniatricyclo[2.2.1.0(2,6)]heptane tribro
mide was isolated rather than the product of bromine addition to the double
bond. The former reacted with the starting alkene in a polar solvent to fo
rm the corresponding monobromide.