Preparation of epiminostearates. Comparison of methods
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The addition of N,N-dichlorourethan (DCU) to internal olefins has been found to be an acceptable reaction leading to the preparation of internal fatty acid aziridines. The yields of isolated epimino derivatives are in the 50–60% range, only slightly lower than those obtained by the iodine isocyanate (INCO) method. In order to compare the stereochemistry of the two methods, an IR spectroscopic procedure was developed which permits an estimation of the relative amounts ofcis- andtrans-aziridines in mixtures of the two. In agreement with literature reports, the INCO method is stereospecific, thecis-olefins giving rise tocis-aziridines and thetrans-olefins formingtrans-aziridines. On the other hand, DCU addition to olefins results in mixtures ofcis- andtrans-aziridines in which the latter isomers predominate. This finding is compatible with the reported free-radical nature of the DCU reaction.
KeywordsMethyl Oleate Ring Closure Aziridine Boron Trifluoride Etherate Methyl Elaidate
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