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Wenker synthesis

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Title: Wenker synthesis  
Author: World Heritage Encyclopedia
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Subject: Nucleophilic substitution, List of organic reactions, Aziridine, Cyclic compound
Publisher: World Heritage Encyclopedia

Wenker synthesis

The Wenker synthesis is an organic reaction converting a beta amino alcohol to an aziridine with the aid 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 the sulfonate salt, This salt is then reacted with sodium hydroxide in the second step forming aziridine. 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 Cyclooctenimine and of cyclooctanone as a result of competing Hofmann elimination.[3]


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