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Synthesis and spectroscopic properties of long‐chain aza, aziridine and azetidine fatty esters
Author(s) -
Lie Ken Jie Marcel S. F.,
SyedRahmatullah M. S. K.
Publication year - 1992
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/bf02636068
Subject(s) - azetidine , aziridine , chemistry , derivative (finance) , infrared spectroscopy , stereochemistry , organic chemistry , ring (chemistry) , financial economics , economics
Reaction of 1‐mesyloxynonane with methyl 8‐aminooctanoate gives methyl 9‐azastearate (I, 20%); treatment of methyl 9(10),10(9)‐azidohydroxyoctadecanoate and methyl 10‐azido‐12‐hydroxyoctadecanoate with triphenylphosphine furnishes the corresponding aziridine derivative (II, 75%) and two geometric azetidine isomers (IIIa and IIIb, 37%), respectively. The aza function in compound I, the aziridine nucleus in compound II and the azetidine system in compounds IIIa, IIIb were characterized by 1 H nuclear magnetic resonance (NMR) and 13 C NMR spectral analysis. The infrared spectral analyses of compounds (I), (II) and (IIIa,IIIb) showed characteristic absorption bands at 3200–3300 cm −1 for the N‐H stretching vibration.