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 form the sulfate monoester. 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 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 using trans-2-aminocyclooctanol, available from reaction of ammonia with the epoxide of cyclooctene, gives a mixture of cyclooctenimine (the Wenker aziridine product) and cyclooctanone (a competing Hofmann elimination product).[3]
^Leighton, Philip A.; Perkins, William A.; Renquist, Melvin L. (1947). "A Modification of Wenker's Method of Preparing Ethyleneimine". J. Am. Chem. Soc. 69 (6): 1540. doi:10.1021/ja01198a512.
^Kashelikar, D. V.; Fanta, Paul E. (1960). "Chemistry of Ethylenimine. VII. Cyclooctenimine or 9-Azabicyclo[6.1.0]nonane". J. Am. Chem. Soc.82 (18): 4927–30. doi:10.1021/ja01503a044.
December 15, 2023
wenker, synthesis, organic, reaction, converting, beta, amino, alcohol, aziridine, with, help, sulfuric, acid, used, industrially, synthesis, aziridine, itself, named, after, henry, wenkerreaction, type, ring, forming, reactionidentifiersorganic, chemistry, po. The Wenker synthesis is an organic reaction converting a beta amino alcohol to an aziridine with the help of sulfuric acid It is used industrially for the synthesis of aziridine itself 1 Wenker synthesisNamed after Henry WenkerReaction type Ring forming reactionIdentifiersOrganic Chemistry Portal wenker synthesis Wenker synthesisThe 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 form the sulfate monoester 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 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 using trans 2 aminocyclooctanol available from reaction of ammonia with the epoxide of cyclooctene gives a mixture of cyclooctenimine the Wenker aziridine product and cyclooctanone a competing Hofmann elimination product 3 9 Azabicyclo 6 1 0 nonane synthesisFurther reading editWenker Henry 1935 The Preparation of Ethylene Imine from Monoethanolamine Journal of the American Chemical Society 57 1 2328 28 doi 10 1021 ja01314a504 References edit Steuerle Ulrich Feuerhake Robert 2006 Aziridines Ullmann s Encyclopedia of Industrial Chemistry Weinheim Wiley VCH doi 10 1002 14356007 a03 239 pub2 Leighton Philip A Perkins William A Renquist Melvin L 1947 A Modification of Wenker s Method of Preparing Ethyleneimine J Am Chem Soc 69 6 1540 doi 10 1021 ja01198a512 Kashelikar D V Fanta Paul E 1960 Chemistry of Ethylenimine VII Cyclooctenimine or 9 Azabicyclo 6 1 0 nonane J Am Chem Soc 82 18 4927 30 doi 10 1021 ja01503a044 Retrieved from https en wikipedia org w index php title Wenker synthesis amp oldid 930538535, wikipedia, wiki, book, books, library,
