Abstract
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 by1H nuclear magnetic resonance (NMR) and13C 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.
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Lie Ken Jie, M.S.F., Syed-Rahmatullah, M.S.K. Synthesis and spectroscopic properties of long-chain aza, aziridine and azetidine fatty esters. J Am Oil Chem Soc 69, 359–362 (1992). https://doi.org/10.1007/BF02636068
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DOI: https://doi.org/10.1007/BF02636068