TheWenker synthesis is anorganic reaction converting a betaamino alcohol to anaziridine with the help ofsulfuric acid. It is used industrially for the synthesis of aziridine itself.^[1]

The original Wenker synthesis of aziridine itself takes place in two steps. In the first stepethanolamine is reacted with sulfuric acid at high temperatures (250 °C) to form thesulfate monoester. This salt is then reacted withsodium hydroxide in the second step forming aziridine. Thebase abstracts an amineproton enabling it todisplace the sulfate group. A modification of this reaction involving lower reaction temperatures (140–180 °C) and therefore reduced charring increases the yield of the intermediate.^[2]

The Wenker synthesis protocol usingtrans-2-aminocyclooctanol, available from reaction ofammonia with theepoxide ofcyclooctene, gives a mixture of cyclooctenimine (the Wenker aziridine product) andcyclooctanone (a competingHofmann elimination product).^[3]

• Wenker, Henry (1935). "The Preparation of Ethylene Imine from Monoethanolamine".Journal of the American Chemical Society.57 (1):2328–28.Bibcode:1935JAChS..57Q2328W.doi:10.1021/ja01314a504.

• Aziridines
• Nitrogen heterocycle forming reactions
• Heterocycle forming reactions
• Substitution reactions
• Name reactions

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