New Type of Skipped Oligoaziridines: Synthesis of New Fatty AcidDerivatives Containing Aziridine Functions

The first successful preparation of the aziridines methyl cis-9,10;cis-12,13-diepiminooctadecanoate (3) derived from linoleic acid, and methyl cis-9,10;cis-12,13;cis-15,16-triepiminooctadecanoate (6) derived from linolenic acid, is reported. Remarkably, the bis- and trisaziridine were obtained in a reaction sequence that consists of only two steps, using technically pure methyl esters of epoxidized sunflower and linseed oil. The conversion of methyl 9,10;12,13-diepoxyoctadecanoate (1), with sodium azide and ammonium chloride in ethanol in the presence of water, yielded the new diazidodihydroxy compound methyl 9(10),12(13)-diazido-10(9),13(12)-dihydroxyoctadecanoate (2) in the first step. 2 was obtained as a regioisomeric mixture. The reaction of 2 with triphenylphosphane led to the bisaziridine 3. The analogous conversion of methyl 9,10;12,13;15,16-triepoxyoctadecanoate (4), via the new triazidotrihydroxy compound methyl 9(10),12(13),15(16)-triazido-10(9),13(12),16(15)-trihydroxyoctadecanoate (5), afforded trisaziridine 6.