Juergen O. Metzger et.al.: New Type of Skipped Oligoaziridines: Synthesis of
New Fatty AcidDerivatives Containing Aziridine Functions
- Author(s): Juergen O. Metzger, Sandra Fuermeier
- Title: New Type of Skipped Oligoaziridines: Synthesis of New Fatty
AcidDerivatives Containing Aziridine Functions
- Date of Upload: 1999
- Article: Eur. J. Org. Chem. 1999, 6612664, Department of Chemistry,
University of Oldenburg, Carl-von-Ossietzky-Str. 9-11, 26129 Oldenburg,
Germany
- Keywords: Aziridines, N-Heterocycles, Fatty acids, sustainable
development, renewable feedstock, vegetable oil, plant oil
- Abstract:
- 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.
- URL: http://www.chemie.uni-oldenburg.de/oc/metzger/publikationen/pdf/81.pdf
(application/pdf)
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