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Isomerization during hydrogenation. II. Methyl cis-10, cis-12-octadecadienoate

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Journal of the American Oil Chemists Society

Summary

Methylcis-10,cis-12-octadecadienoate was prepared and found to have an ultraviolet absorption peak at 235 mµ, α=95. The infrared spectrum revealed no diagnostic peaks for thecis,cis conjugated system.

The hydrogenation of the ester showed that when one mole of hydrogen was added, 1–2, 1–4, and 3–4 addition took place with equal ease to produce an equimolar mixture ofcis-10-,trans-11-, andcis-12-octadecenoates. An explanation of the reaction is offered on the basis of the structure of the diene system.

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References

  1. Allen, R. R., and Kiess, A. A., J. Am. Oil Chemists’ Soc.,32, 400 (1955).

    CAS  Google Scholar 

  2. Allen, R. R., J. Am. Oil Chemists’ Soc.,32, 671 (1955).

    CAS  Google Scholar 

  3. Black, H. K., and Weedon, B. C. L., J. Chem. Soc.,1953, 1785.

  4. Crombie, L., J. Chem. Soc.,1955, 1007.

  5. Hilditch, T. P., Vidyarthi, N. L., Proc. Ray. Soc. (London),A122, 552–570 (1929).

    CAS  ADS  Google Scholar 

  6. Jackson, J. E., Paschke, R. F., Tolberg, Wesley, Boyd, H. M., and Wheeler, D. H., J. Am. Oil Chemists’ Soc.,29, 229 (1952).

    CAS  Google Scholar 

  7. Jeffry, G. H., and Vogel, A. I., J. Chem. Soc.,1948, 674.

  8. Lindlar, H., Helv. Chim. Acta.35, 446 (1952).

    Article  CAS  Google Scholar 

  9. Nichols, P. L. Jr., Herb, S. F., and Riemenschneider, R. W., J. Am. Chem. Soc.,73, 247 (1951).

    Article  CAS  Google Scholar 

  10. Sheppard, N., and Simpson, D. M., Quart. Rev. (London),6, 1 (1952).

    CAS  Google Scholar 

  11. Zechmeister, L., Le Rosen, A. L., Schroeder, W. A., Polgar, A., and Pauling, L., J. Am. Chem. Soc.,65, 1940 (1943).

    Article  CAS  Google Scholar 

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Allen, R.R. Isomerization during hydrogenation. II. Methyl cis-10, cis-12-octadecadienoate. J Am Oil Chem Soc 33, 301–304 (1956). https://doi.org/10.1007/BF02639333

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  • DOI: https://doi.org/10.1007/BF02639333

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