Reactions are typically conducted in polar solvents such as alcohols. Even pyridines, which are considerably less nucleophilic than typical tertiary amines, react with dichloromethane at room temperature over a period of several days to weeks to give bis(pyridinium)methane salts. In addition to solvent and alkylating agent, other factors strongly influence the reaction. In one particular
macrocycle system the reaction rate is not only accelerated (150000 fold compared to
quinuclidine) but the halide order is also changed ==History==