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Fatty acids: part 27. Olefin inversion involving unsaturated fatty esters

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Journal of the American Oil Chemists’ Society

Abstract

Unsaturated long chain fatty esters gave the corresponding bromochloro ester derivatives when treated with N-bromosuccinimide and hydrogen chloride. Treatment of the intermediate halo esters with sodium iodide furnished the same positional unsaturated fatty ester isomers, but of opposite geometric configuration. This olefin isomerization method was found to be high yielding, stereospecific and to cause no double bond migration.

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References

  1. Lie Ken Jie, M.S.F., and F. Ahmad, JAOCS 60:1783 (1983).

    Google Scholar 

  2. Sommerfeld, M., Prog. Lipid Res. 22:221 (1983).

    Article  CAS  Google Scholar 

  3. Devinat, G., L. Scamaroni and M. Naudet, Rev. Fr. Corps Gras 27:283 (1980). [Chem. Abstr. 93:166338m (1980)].

    CAS  Google Scholar 

  4. Fitzpatrick, J.D., and M. Orchin, J. Am. Chem. Soc. 79:4765 (1957).

    Article  CAS  Google Scholar 

  5. Litchfield, C., J.E. Lord, A.F. Isbell and R. Reiser, JAOCS 40:553 (1963).

    CAS  Google Scholar 

  6. Kasse, J.P., J. Nichols and G.O. Burr, J. Am. Chem. Soc. 63:1060 (1941).

    Article  Google Scholar 

  7. Sgoutas, D.S., and F.A. Kummerov, Lipids 4:283 (1969).

    Article  CAS  Google Scholar 

  8. Sonnet, P.E., Tetrahedron 36:557 (1980).

    Article  CAS  Google Scholar 

  9. Lam, C.H., and M.S.F. Lie Ken Jie, J. Chromatog. 115:559 (1975); 117:365 (1976); 121:303 (1976).

    Article  CAS  Google Scholar 

  10. Hageman, H.J., and E. Havinga, Rec. Trav. Chim. 85:1141 (1966).

    Article  CAS  Google Scholar 

  11. Hine, J., and W.H. Brader Jr., J. Am. Chem. Soc. 77:361 (1955).

    Article  CAS  Google Scholar 

  12. Schmid, H., and P. Karrer, Ibid. 29:573 (1946).

    CAS  Google Scholar 

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Lie Ken Jie, M.S.F., Chan, M.F. Fatty acids: part 27. Olefin inversion involving unsaturated fatty esters. J Am Oil Chem Soc 62, 109–110 (1985). https://doi.org/10.1007/BF02541504

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  • DOI: https://doi.org/10.1007/BF02541504

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