Wenker synthesis

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



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 the sulfonate salt, This salt is then reacted with sodium hydroxide in the second step forming azirine. The base abstracts an amine proton enabling it to displace the sulfonate group. A modification of this reaction involving lower reaction temperatures (140 - 180°C) and therefore reduced charring increases the yield of the intermediate.

Starting from cyclooctene oxide, trans-2-Aminocyclooctanol gives a mixture of Cycloöctenimine and of cyclooctanone as a result of competing Hofmann elimination.