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Aziridine is an organic compound consisting of the three-membered heterocycle C 2 H 5 N. [ 5 ] [ 6 ] It is a colorless, toxic, volatile liquid that is of significant practical interest. [ 7 ] Aziridine was discovered in 1888 by the chemist Siegmund Gabriel . [ 8 ]
In organic chemistry, aziridines are organic compounds containing the aziridine functional group (chemical structure (R−) 4 C 2 N−R), a three-membered heterocycle with one amine (>NR) and two methylene bridges (>CR 2). [2] [3] [4] The parent compound is aziridine (or ethylene imine), with molecular formula C 2 H 4 NH.
Propyleneimine (or propylene imine) is the organic compound with the formula CH 3 CH(NH)CH 2. It is a secondary amine and the smallest chiral aziridine (ring containing C 2 N). It is a flammable colorless liquid. Its derivatives, copolymers and oligomers, are of commercial interest. [4]
The general structure of an imine. In organic chemistry, an imine (/ ... Thus, ethylenimine is the three-membered ring species aziridine C 2 H 4 NH. [8]
The synthesis of aziridines from imines is another important application of the Johnson–Corey–Chaykovsky reaction and provides an alternative to amine transfer from oxaziridines. Though less widely applied, the reaction has a similar substrate scope and functional group tolerance to the carbonyl equivalent.
The Blum–Ittah aziridine synthesis, also known as the Blum–Ittah-Shahak aziridine synthesis [1] or simply the Blum aziridine synthesis is a name reaction of organic chemistry, for the generation of aziridines from oxiranes.
Ring opening of aziridine to form azomethine ylide. In this ring opening reaction, there is an issue of torquoselectivity . Electronegative substituents prefer to rotate outwards, to the same side as the R substituent on the nitrogen, whereas electropositive substituents prefer to rotate inwards.
Polyethylenimine (PEI) or polyaziridine is a polymer with repeating units composed of the amine group and two carbon aliphatic CH 2 CH 2 spacers. Linear polyethyleneimines contain all secondary amines, in contrast to branched PEIs which contain primary, secondary and tertiary amino groups.