Die Struktur einer stabilen dipolaren Verbindung aus 2,2-Dimethyl-3-dimethylamino-2H-azirin und Benzoylisothiocyanat

Benzoylisothiocyanate and 2,2-dimethyl-3- dimethylamino-2H-azirine (1) react to give the dipolar compound 4,4-dimethyl-2-thiazolin-5- dimethyliminium-2-benzcarboxamidate (2), whose structure has been proved by X-ray analysis. Compound 2, upon addition of water, yields the thiourea derivative 3, whereas by acid catalyzed hydrolysis the thiazolinone derivative 4 is formed. The dipolar structure 2 is also existent in organic solvents like dimethylsulfoxide or chloroform