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The Wenker synthesis is an organic reaction converting a beta amino alcohol to an aziridine with the aid of sulfuric acid. Organic reactions are Chemical reactions involving Organic compounds The basic Organic chemistry reaction types are Addition reactions Elimination Amino alcohols are Organic compounds that contain both an Amine Functional group and an Alcohol functional group Aziridines are a group of Organic compounds sharing the aziridine Functional group which is a three membered Heterocycle with one Amine group Sulfuric (or sulphuric acid, H 2 S[[oxygen O]]4 is a strong Mineral acid. [1]

Wenker synthesis

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 azirine. Ethanolamine, also called 2-aminoethanol or monoethanolamine (often abbreviated as ETA or MEA) is an Organic chemical compound Sulfuric (or sulphuric acid, H 2 S[[oxygen O]]4 is a strong Mineral acid. A sulfonate ion is an ion that contains the -S(=O2-O&minus Functional group. Sodium hydroxide ( Na[[hydroxide OH]]) also known as Lye, caustic soda and (incorrectly according to IUPAC nomenclature The base abstracts an amine proton enabling it to displace the sulfonate group. In Chemistry, a base is most commonly thought of as an aqueous substance that can accept Protons This refers to the Brønsted-Lowry theory of acids and In organic and Inorganic chemistry, nucleophilic substitution is a fundamental class of Substitution reaction in which an "electron rich" 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. An epoxide is a cyclic Ether with only three ring atoms This ring approximately is an Equilateral triangle, i Hofmann elimination (also known as exhaustive methylation) is a process where an Amine is reacted to create a tertiary amine and an Alkene by treatment [3]

9-Azabicyclo[6.1.0]nonane synthesis

References

  1. ^ Henry Wenker (1935). "The Preparation of Ethylene Imine from Monoethanolamine". Journal of the American Chemical Society 57 (1): 2328–2328. The Journal of the American Chemical Society (usually abbreviated as J doi:10.1021/ja01314a504. A digital object identifier ( DOI) is a permanent identifier given to an Electronic document.  
  2. ^ A Modification of Wenker's Method of Preparing Ethyleneimine Philip A. Leighton, William A. Perkins, and Melvin L. Renquist J. Am. Chem. Soc.; 1947; 69(6) pp 1540 - 1540. The Journal of the American Chemical Society (usually abbreviated as J (doi:10.1021/ja01198a512)
  3. ^ Chemistry of Ethylenimine. A digital object identifier ( DOI) is a permanent identifier given to an Electronic document. VII. Cycloöctenimine or 9-Azabicyclo[6. 1. 0]nonane D. V. Kashelikar, Paul E. Fanta J. Am. Chem. Soc.; 1960; 82(18); 4927-4930. The Journal of the American Chemical Society (usually abbreviated as J (doi:10.1021/ja01503a044)
A digital object identifier ( DOI) is a permanent identifier given to an Electronic document.
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