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Preparation of epiminostearates. Comparison of methods
Author(s) -
Foglia T. A.,
Maerker G.,
Smith G. R.
Publication year - 1970
Publication title -
journal of the american oil chemists' society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.512
H-Index - 117
eISSN - 1558-9331
pISSN - 0003-021X
DOI - 10.1007/bf02632470
Subject(s) - stereospecificity , chemistry , cis–trans isomerism , isocyanate , organic chemistry , catalysis , polyurethane
Abstract 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 of cis ‐ and trans ‐aziridines in mixtures of the two. In agreement with literature reports, the INCO method is stereospecific, the cis ‐olefins giving rise to cis ‐aziridines and the trans ‐olefins forming trans ‐aziridines. On the other hand, DCU addition to olefins results in mixtures of cis ‐ and trans ‐aziridines in which the latter isomers predominate. This finding is compatible with the reported free‐radical nature of the DCU reaction.