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Oxidative cyclization of 1-octadecanol and hydroxy fatty esters with lead tetraacetate

  • Technical
  • Published:
Journal of the American Oil Chemists Society

Abstract

Oxidative cyclization of methyl 2-hydroxyoctadecanoate, methyl 10-hydroxyundecanoate and 1-octadecanol produced a good yield of the corresponding tetrahydrofuran (THF) derivatives characterized successively as methyl 2,5-epoxyoctadecanoate, methyl 7,10-epoxyundecanoate and 1,4-epoxyoctadecane. The structure of these cyclic derivatives have been established by elemental analyses and spectral studies.

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Hashmi, M., Khan, M., Ahmad, M.S. et al. Oxidative cyclization of 1-octadecanol and hydroxy fatty esters with lead tetraacetate. J Am Oil Chem Soc 61, 1024–1027 (1984). https://doi.org/10.1007/BF02636209

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  • DOI: https://doi.org/10.1007/BF02636209

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