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Synthesis of 2, 3 fatty aziridines
Author(s) -
Rauf A.,
Ahmad M. S.,
Ahmad F.,
Osman S. M.
Publication year - 1984
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/bf02542176
Subject(s) - ammonia , chemistry , elemental analysis , medicinal chemistry , infrared spectroscopy , infrared , organic chemistry , physics , optics
A new route for the synthesis of 2,3‐aziridines is described. The reaction of methyl 2,3‐dibromohexadecanoate (II) with ammonia at 0 C gave methyl 2‐bromohexadec‐2‐enoate (III, ca. 93%). Compound III, on further treatment with ammonia at 25 C, gave methyl 2‐aminohexadec‐2‐enoate (IV, ca. 5%), methyl trans ‐2,3‐epiminohexadecanoate (V, ca. 64%), methyl cis ‐2,3‐epiminohexadecanoate (VI, ca 24%) and trans ‐2,3‐epiminohexadecamide (VII, ca 3%). The structures were established with the help of elemental analyses and infrared (IR), nuclear magnetic resonance (NMR) and mass spectral analyses.