Structure of dibromoticonine, a bromination product of nicotine
Abstract
The fate of the pyrrolidine ring of nicotine on its oxidative bromination to dibromoticonine has been re-examined. From chemical and spectral (including 13C n.m.r.) properties dibromoticonine is now established as 3,4-dibromo-5-hydroxy-1-methyl-5-(3-pyridyl)-Δ3-pyrrolin-2-one. The bromine atoms can be selectively replaced by hydrogen under proper reductive conditions to give the isomeric monobromoticonines.