Addition of phthalimidonitrene to acetylenic fatty acid esters: Synthesis of long‐chain 2‐phthalimido‐2H‐azirines
- 1 January 1986
- journal article
- Published by Wiley in Journal of Oil & Fat Industries
- Vol. 63 (1) , 92-95
- https://doi.org/10.1007/bf02676130
Abstract
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.Keywords
This publication has 11 references indexed in Scilit:
- Reactive intermediates. Part XXII. Formation of 2H-azirines by oxidation of N-aminophthalimide in the presence of alkynesJournal of the Chemical Society, Perkin Transactions 1, 1973
- Preparation and reactions of fatty acid azirinesJournal of Oil & Fat Industries, 1972
- Formation of 2H-azirines by the pyrolysis of 1,2,3-triazolesJournal of the Chemical Society D: Chemical Communications, 1971
- Azirine formation by decomposition of terminal vinyl azidesTetrahedron Letters, 1969
- Small Antiaromatic RingsAngewandte Chemie International Edition in English, 1968
- General synthesis of vinyl azides from olefins. Stereochemistry of elimination from .beta.-iodo azidesThe Journal of Organic Chemistry, 1968
- Antiaromaticity of cyclopropenyl anionsJournal of the American Chemical Society, 1967
- Hydration of Acetylenic Fatty AcidsFette, Seifen, Anstrichmittel, 1967
- 4. Chemiluminescent organic compounds. Part I. Isomeric simple and complex hydrazides of phthalic acid and mode of formation of phthalazine and isoindole ringsJournal of the Chemical Society, 1937
- Über den Reaktionsverlauf einer neuen Art von Umlagerung bei Ketoximen. IIIEuropean Journal of Organic Chemistry, 1932