Menshutkin reaction

[1] Some phase transfer catalysts (PTC) can be prepared according to the Menshutkin reaction, for instance the synthesis of triethyl benzyl ammonium chloride (TEBA) from triethylamine and benzyl chloride: Reactions are typically conducted in polar solvents such as alcohols.

As is typical for an SN2 process, benzylic, allylic, and α-carbonylated alkyl halides are excellent reactants.

Highly nucleophilic tertiary amines like DABCO will react with dichloromethane at room temperature overnight and at reflux (39-40 °C) over several hours to give the quaternized product (see the article on Selectfluor).

Due to steric hindrance and unfavorable electronic properties, chloroform reacts very slowly with tertiary amines over a period of several weeks to months.

[2] 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.