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Epimino derivatives from β‐lodoazides
Author(s) -
Foglia T. A.,
Barr P. A.,
Schmeltz I.
Publication year - 1973
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/bf02641357
Subject(s) - chemistry , yield (engineering) , hydride , aziridine , olefin fiber , aluminum hydride , alcohol , adduct , catalysis , derivative (finance) , lithium (medication) , organic chemistry , catalytic hydrogenation , medicinal chemistry , metal , materials science , ring (chemistry) , medicine , methoxide , economics , financial economics , metallurgy , endocrinology
The preparation of the epimino derivatives of oleyl alcohol and methyl oleate by a two‐step procedure has been studied. The procedure utilized the addition of iodine azide to the unsaturated compound, followed by reductive cyclization to the aziridine. For the latter step, several hydride‐reducing agents and direct hydrogenation over metal catalysts were investigated. Comparison of the various methods studied showed that the best yields of epimino derivatives were obtained with lithium aluminum hydride, whereas direct hydrogenation gave the poorest yield. The reaction of the β‐iodoazide adducts with trimethyl phosphite was also investigated and was shown to give rise to the dialkylphosphonoaziridinyl derivative of the starting olefin.