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New Type of Skipped Oligoaziridines: Synthesis of New Fatty AcidDerivatives Containing Aziridine Functions
Author(s) -
Metzger Jürgen O.,
Fürmeier Sandra
Publication year - 1999
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(199903)1999:3<661::aid-ejoc661>3.0.co;2-v
Subject(s) - chemistry , aziridine , sodium azide , linoleic acid , linseed oil , organic chemistry , ethanol , sunflower oil , medicinal chemistry , fatty acid , ring (chemistry) , biochemistry
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 .