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Wenker synthesisThe Wenker synthesis is an organic reaction converting a beta amino alcohol to an aziridine with the aid of sulfuric acid.[1] Additional recommended knowledgeThe 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.[2] Starting from cyclooctene oxide, trans-2-Aminocyclooctanol gives a mixture of Cycloöctenimine and of cyclooctanone as a result of competing Hofmann elimination.[3] References
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This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Wenker_synthesis". A list of authors is available in Wikipedia. |