Wenker synthesis

The Wenker synthesis is an organic reaction converting a beta amino alcohol to an aziridine with the help of sulfuric acid.

[1] The original Wenker synthesis of aziridine itself takes place in two steps.

In the first step ethanolamine is reacted with sulfuric acid at high temperatures (250 °C) to form the sulfate monoester.

The base abstracts an amine proton enabling it to displace the sulfate group.

[2] The Wenker synthesis protocol using trans-2-aminocyclooctanol, available from reaction of ammonia with the epoxide of cyclooctene, gives a mixture of cyclooctenimine (the Wenker aziridine product) and cyclooctanone (a competing Hofmann elimination product).