Posted by Admin on August, 29, 2019
Aziridine is a special organic compound which falls under the functional group of Aziridine. It is a three-membered heterocyclic compound which owns one anime group along with two methylene bridges. Ethylene imine is known as its parent compound having a molecular formula C-2H-5N.
Structure of the compound
The angles of the bond in Aziridine are about sixty degrees. It is comparatively lesser than the normal bond angle of hydrocarbon, which is 109.5°. This leads to a strain in the angle, especially in the comparable molecules of both cyclopropane as well as ethylene oxide.
Using the model of the banana bond, the bonding of Aziridine compound can be explained. Compared to acyclic aliphatic animes, Aziridine is less basic, having a pH of 7.9 in case of conjugate acid. It is due to the presence of the free electron pair of nitrogen.
In this case, the strain of the angle of Aziridine compound also increases the number of barriers to the inversion of nitrogen. The usual height of the barriers allows the isolation of the invertomers, which are separate.
Synthesis Of Aziridine Compound
There are a variety of syntheses procedures of Aziridine practically used the Aziridine Manufacturers which can be described as:
In this process, a particular functional anime group displaces its adjacent halide in a special intramolecular nucleophilic substitution reaction which leads to the generation of Aziridine. The amino alcohols present own the same kind of reactivity. However, the hydroxyl group needs to be converted first to form a proper group. The process of cyclization of the amino alcohol is known as Wenker Synthesis. When the same is done using a haloamine, it is known as the Gabriel Ethylenediamine method.
Addition of Nitrene
The addition of Nitrene to the alkenes is one of the most properly-established methods for the synthesis of the Aziridine compound. The processes of photolysis, or more commonly thermolysis of the azide, is considered as one of the good ways of generating nitrenes. The Nitrene compound is sometimes even prepared in the same manner using compounds of iodosobenzenediacetate along with sulfonamides, orethoxy carbonyl nitrene. These compounds belong to the N-sulfonyloxy precursor.
Decomposition of Triazoline
In this process, the triazoline compound undergoes a properly arranged thermal treatment, or commonly photolysis. This helps in expelling the nitrogen compound, leading to the production of Aziridine. As per experts, triazolinecan easily be generated with the addition of little alkenes with azides.
From The Epoxides
This is one of the most common methods, which involve a special reaction known as the ring-opening reaction. This takes place between epoxide and sodium azide, which is usually followed by the reduction reaction of the azides with triphenylphosphine. This reaction is accompanied by an expulsion of the nitrogen gas too.
Apart from these processes of synthesis, Aziridine compound can also be synthesized using oximes, the special Hoch Campbell Ethylenediamine Synthesis and also from the alkenes which make use of DPH. As per the Aziridine Manufacturers, out of all, the process of synthesis of Aziridine by using alkenes with DPH brings out the best results. It leads to a good yield in a time-saving process.