Sommelet reaction

[1][2] It is named after the French chemist Marcel Sommelet, who first reported the reaction in 1913.

The benzyl halide 1 reacts with hexamine to a quaternary ammonium salt 3, each time just alkylating one nitrogen atom.

Then the benzylammonium undergoes an acid-catalyzed hydrolysis process.

Depending on the hydrolysis conditions, the hexamine unit might instead break apart, leaving a benzyl amine (the Delépine reaction).

The reaction can also be applied to the oxidation of benzylic amines.