Addition of phthalimidonitrene to acetylenic fatty acid esters: synthesis of long-chain 2-phthalimido-2H-azirines

Lead tetraacetate (LTA) oxidations of N-aminophthalimide in the presence of acetylenic fatty acid esters have resulted in the formation of corresponding 1H-azirines that spontaneously rearranged to give 2H-azirines in moderate yields. 2H-Azirine derivatives (IV, V and VI) of acetylenic fatty acid esters, methyl 10-undecynoate (I), methyl 9-undecynoate (II) and methyl 9-octadecynoate (III), respectively, have been prepared and characterized with the help of spectral and micro analyses.