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The Wenker synthesis is an 
The original Wenker synthesis of aziridine itself takes place in two steps. In the first step 
organic reaction
Organic reactions are chemical reactions involving organic compounds. The basic organic chemistry reaction types are addition reactions, elimination reactions, substitution reactions, pericyclic reactions, rearrangement reactions, mechanistic organ ...
converting a beta amino alcohol to an aziridine
Aziridine is an organic compound consisting of the three-membered heterocycle . It is a colorless, toxic, volatile liquid that is of significant practical interest. Aziridine was discovered in 1888 by the chemist Siegmund Gabriel. Its deriva ...
with the help of sulfuric acid
Sulfuric acid (American spelling and the preferred IUPAC name) or sulphuric acid (English in the Commonwealth of Nations, Commonwealth spelling), known in antiquity as oil of vitriol, is a mineral acid composed of the elements sulfur, oxygen, ...
. It is used industrially for the synthesis of aziridine itself.
The original Wenker synthesis of aziridine itself takes place in two steps. In the first step ethanolamine
Ethanolamine (2-aminoethanol, monoethanolamine, ETA, or MEA) is a naturally occurring organic chemical compound with the formula or . The molecule is bifunctional, containing both a primary amine and a primary alcohol. Ethanolamine is a colorl ...
is reacted with sulfuric acid at high temperatures (250 °C) to form the sulfate
The sulfate or sulphate ion is a polyatomic anion with the empirical formula . Salts, acid derivatives, and peroxides of sulfate are widely used in industry. Sulfates occur widely in everyday life. Sulfates are salts of sulfuric acid and many ...
monoester. This salt is then reacted with sodium hydroxide
Sodium hydroxide, also known as lye and caustic soda, is an inorganic compound with the formula . It is a white solid ionic compound consisting of sodium cations and hydroxide anions .
Sodium hydroxide is a highly corrosive base (chemistry), ...
in the second step forming aziridine. The base abstracts an amine proton enabling it to displace 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.
The Wenker synthesis protocol using ''trans''-2-aminocyclooctanol, available from reaction of ammonia
Ammonia is an inorganic chemical compound of nitrogen and hydrogen with the chemical formula, formula . A Binary compounds of hydrogen, stable binary hydride and the simplest pnictogen hydride, ammonia is a colourless gas with a distinctive pu ...
with the epoxide
In organic chemistry, an epoxide is a cyclic ether, where the ether forms a three-atom ring: two atoms of carbon and one atom of oxygen. This triangular structure has substantial ring strain, making epoxides highly reactive, more so than other ...
of cyclooctene, gives a mixture of cyclooctenimine (the Wenker aziridine product) and cyclooctanone (a competing Hofmann elimination product).
Further reading
*References
{{DEFAULTSORT:Wenker Synthesis Aziridines Nitrogen heterocycle forming reactions Heterocycle forming reactions Substitution reactions Name reactions