Ethylene derivatives aziridines

Similarly, another accident occurred when metallic silver came into contact with aziridine. According to the authors of the report, the accident was interpreted by the formation of an aziridine silver derivative. Comparing this behaviour with the one of ethylene oxide when silver is present, a danger which is of the same nature is demonstrated. The interpretation that had been given at the time was based on the presence of acetylene in ethylene oxide, whose silver derivatives are very sensitive explosives. It may be that acetylene traces were present in aziridine although none of the authors mentioned such as possibility as far as we know. 

An important method for preparing aziridine (ethylene imine) and its derivatives is to cyclize the sulfuric esters of ethanolamines by heating them... 

Lead tetraacetate Reactions via aminonitrenes Aziridines from ethylene derivs. 

Aziridines from ethylene derivatives via quaternary hydrazinium salts... 

Diphenyliodonium iodide Ethylene derivatives from aziridines... 

All lene Oxides and Aziridines. Alkyleneamines react readily with epoxides, such as ethylene oxide [75-21-8] (EO) or propylene oxide [75-56-9] (PO), to form mixtures of hydroxyalkyl derivatives. Product distribution is controlled by the amine to epoxide mole ratio. If EDA, which has four reactive amine hydrogens, reacts at an EDA to EO mole ratio which is greater than 1 4, a mixture of mono-, di-, tri,-, and tetrahydroxyethyl derivatives of EDA are formed. A 10 1 EDA EO feed mole ratio gives predominandy 2-hydroxyethylethylenediamine [111-41-1], the remainder is a mixture of bis-(2-hydroxyethyl)ethylenediamines (7). If the reactive NH to epoxide feed mole ratio is less than one and, additionally, a strong basic catalyst is used, then oxyalkyl derivatives, like those shown for EDA and excess PO result (8,9). 

Cyclophosphamide (72) was made as a latent form of nitrogen mustard with fairly low toxicity. It undergoes oxidation by microsomes in the liver and then breaks down to give much more reactive derivatives of 2,2 -dichlorodiethylamine (Scheme 3). Several aziridines are used as alkylating agents. They include triethylenemelamine (73), triaziquone (74), TEPA (triethylenephosphoramide) (75 X = O) and thio-TEPA (75 X = S). Ethylene oxide... 

One of the features of a,/3-unsaturated ketones is the presence of two electrophilic centers. Because of this feature, reactions with binucleophiles can proceed as a 1,2-addition or as a 1,4-addition. Regarding three-membered nitrogen-containing heterocycles formed from a,/3-unsaturated ketones and their derivatives, the unsaturated ketone acts either as a 1,2-bielectrophile (substituted ethylene), which leads to the formation of ethyleneimines, or as a 1,4-bielectrophile, giving rise to either bi- or tricyclic aziridines. Hence, the present chapter is divided into two parts, one which is entirely dedicated to aziridinyl ketones and the other to bi- and tricyclic aziridines. 

Aminoquinazolinone derivatives were oxidized with the optically active oxidant lead tetra-(S)-2-methylbutanoate in the presence of excess styrene, E)-, 2-diphenylethylene and dimethyl fumarate. The aziridine was obtained with asymmetric induction only from ( )- 1,2-diphenyl-ethylene, but the enantiomeric excess was not reported31. 

N-nilrosoaniline in fair yield. Bumgardner attempted to convert aziridine into the N-nitroso derivative by this method but isolated only ethylene and nitrous oxide. 

The derivatives of ethylene oxide and aziridine can be used to build macrocycles. Substituted aziridine or ethylene oxide self-condenses on ring opening to form cyclic trimers, tetramers, and so on (Dale and Daasvatn, 1976 Dale et al., 1974 Hansen and Burg, 1968 Tsuboyama et al., 1970). The size of the macrocycle depends mainly on what starting material is used. In the case of N-benzylaziridine, the macrocycle formed was the tetraaza-12-crown-4. 

These species are isoelectronic with carbenes. The parent compound is nitrene NH (also known as imidogen, azene, or imene), which is formed when hydrazoic acid is irradiated with UV Hght in an aromatic solvent, which produces a small amount of primary aromatic amine. In the presence of ethylene, nitrene is trapped to form aziridine (Scheme 6.1). Nitrenes are also referred to as derivatives of imidogens as aminyls, azene, azylene, azacarbene, imene, or imines. 

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