Structure of products of the reaction of 2-cyanoaziridine with carbonyl compounds

Article abstract of DOI:10.1007/BF00698898

The structure of azimexone (3), the product of the reaction of 2-cyanoaziridine with acetone, was confirmed on the basis of 1H and 13C NMR spectra.The formation of this product is accounted for by the α-aziridinoalkylating action of an intermediate containing a good leaving iminoyloxy group.Similar reactions were observed for 1-chloromethylaziridine and a 1-aziridinylmethylammonium salt (6), but not for 1-methoxymethylaziridine (7) and 1-aziridinemethanol. - Key words: 2-(2-cyanoaziridino)-2-(2-carbamoylaziridino)propane; 1-tert-butyl-2-carbamoylaziridine; α-1-aziridinoalkylation; 1H and 13C NMR spectra.