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Ultrasound in lipid chemistry, cyclopropanation of unsaturated fatty esters and triglycerides

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Journal of the American Oil Chemists’ Society

Abstract

Concomitant ultrasonic irradiation during the Simmons-Smith reaction facilitated the cyclopropanation of ethylenic fatty esters and triglycerides. Methyl ricinoleate furnished predominantly the corresponding hydroxy cyclopropanoid ester when the reaction was carried out at 85–95 C under ultrasound in the presence of zinc, while a C18 furanoid fatty ester gave a novel tricyclo derivative (methyl 9,12-epoxy-9,10;11,12-dimethanooctadecanoate).

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References

  1. Lie Ken Jie, M.S.F., J. Bus, A. Groenewegen and I. Sies,J. Chem. Soc. Perk. Trans II, 1275 (1986).

  2. Bremner, D.,Chem. Br. 22:633 (1986).

    CAS  Google Scholar 

  3. Repic, O., and S. Vogt,Tet. Letters 23:2729 (1982).

    Article  CAS  Google Scholar 

  4. Repic, O., P.G. Lee and U. Giger,Org. Prep. Proced. Int. 16:25 (1984).

    Article  CAS  Google Scholar 

  5. Simmons, H.E., T.L. Cairns, S.A. Vladuchick and C.M. Hoiness,Org. Reactions 20:1 (1973).

    CAS  Google Scholar 

  6. Rieck, R.D., P.T.-J. Li, T.P. Burns and S.T. Uhm,J. Org. Chem. 46:4324 (1981).

    Article  Google Scholar 

  7. Friedrich, E.C., J.M. Domek and R.Y. Pong, Ibid.:4640 (1985).

    Article  CAS  Google Scholar 

  8. Ansari, F.A., S.M. Osman and M.R. Subbaram,Indian J. Chem. 11:1053 (1973).

    CAS  Google Scholar 

  9. Ahmad, M.S. Jr., and S.M. Osman,J. Am. Oil Chem. Soc. 57:363 (1980).

    CAS  Google Scholar 

  10. Asselineau, J., inThe Bacterial Lipids, Holden-Day Inc., San Francisco, CA, 1966, pp. 92–94.

    Google Scholar 

  11. Lie Ken Jie, M.S.F., and M.F. Chan,J. Chem. Soc. Chem. Commun. 78 (1977).

  12. Suslick, K.S., J.W. Goodale, P.F. Schubert and H.H. Wang,J. Am. Chem. Soc. 105:5781 (1983).

    Article  CAS  Google Scholar 

  13. Brown, H.C., C.P. Garg and K.T. Liu,J. Org. Chem. 36:387 (1971).

    Article  CAS  Google Scholar 

  14. Dauben, W.G., and G.H. Berezin,J. Am. Chem. Soc. 85:468 (1963).

    Article  CAS  Google Scholar 

  15. Lie Ken Jie, M.S.F., and C.H. Lam,Chem. Phys. Lipids 20:1 (1977).

    Article  Google Scholar 

  16. Still, W.C., M. Khan and A. Mitra,J. Org. Chem. 43:2923 (1978).

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Department of Chemistry, University of Hong Kong, Pokfulam Road, Hong Kong

    Marcel S. F. Lie Ken Jie & Wilson L. K. Lam

Authors
  1. Marcel S. F. Lie Ken Jie
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  2. Wilson L. K. Lam
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Lie Ken Jie, M.S.F., Lam, W.L.K. Ultrasound in lipid chemistry, cyclopropanation of unsaturated fatty esters and triglycerides. J Am Oil Chem Soc 65, 118–121 (1988). https://doi.org/10.1007/BF02542561

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  • DOI: https://doi.org/10.1007/BF02542561

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