Synthesis and spectroscopic properties of long‐chain aza, aziridine and azetidine fatty esters

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 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.