No abstract

iV-Aryl-l-aziridinecarboximidoyl chlorides prepared from aziridines and aryl isocyanide dichlorides undergo facile rearrangement to carbodiimides. The aziridines and carbodiimides were converted to imidazolidinetriones by treatment with oxalyl chloride followed by hydrolysis. The rearrangement to carbodiimides occurs in the neat liquid or in solution and is catalyzed by strong Br0nsted acids; kinetic evidence suggests cationic intermediates formed by acid-assisted heterolysis of the C-Cl bond.Recently we described a novel class of aziridine isomerizations which formally involved a 1,4 shift of X accompanied by the formation of an -N=Y=Z group.

No abstract

N‐(m‐Nitrophenyl)‐1‐aziridincarbonsäureiminoäther (Ia) und das entsprechende Säurechlorid (Ib) ergeben mit Oxalylchlorid über diskutierte Zwischenstufen das 1‐β‐Chloräthyl‐3‐m‐nitrophenyl‐imidazolidin‐2 ,4,5‐trion (II).

Aziridine (I) und Isocyaniddichloride (II) geben die Substitutionsprodukte (III), die thermisch oder mit Säuren zu den Carbodiimiden (IV) umgelagert werden können.