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Geometrical and positional isomerization of alkenyl acetates produced by hydrogenation of alkynyl acetates over palladium metal catalysts

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Abstract

Alkenyl acetates containing both geometrical isomers can be produced by a single controlled catalytic hydrogenation of the corresponding alkynyl acetate. The hydrogenation is capable of yielding formulations containing up to 60% trans isomer; the reduction is attended by positional isomerization in both geometrical isomers.

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References

  • Augustine, R. 1965. Catalytic Hydrogenation. Marcel Dekker, New York.

    Google Scholar 

  • Beroza, M., andBierl, B.A. 1967. Rapid determination of olefin position in organic compounds in microgram range by ozonolysis and gas chromatography.Anal. Chem., 39:1131–1135.

    Google Scholar 

  • Corey, E.J., andSuggs, J.W. 1975. Pyridinium chlorochromate. An efficient reagent for oxidation of primary and secondary alcohols to carbonyl compounds.Tetrahedron Lett. 31:2647–2650.

    Google Scholar 

  • Dobson, N.A., Eglinton, G., Krishnamurti, M., Raphael, R.A., andWillis, R.G. 1961. Selective catalytic hydrogenation of acetylenes.Tetrahedron 16:16–24.

    Google Scholar 

  • Henrick, C.A. 1977. The synthesis of insect sex pheromones.Tetrahedron 33:1845–1889.

    Google Scholar 

  • Houx, M.W.H., Voerman, S., andJongen, W.M.F. 1974. Purification and analysis of synthetic insect sex attractants by liquid chromatography on silver loaded resin.J. Chromatogr. 96:25–32.

    PubMed  Google Scholar 

  • Jacobson, M. 1972. Insect Sex Pheromones, pp. 228–242. Academic Press, New York.

    Google Scholar 

  • Roelofs, W.T., andCardé, R.T. 1977. Responses of lepidoptera to synthetic sex pheromone chemicals and their analogues.Ann. Rev. Entomol. 22:377–405.

    Google Scholar 

  • Roelofs, W.T., andCardÉ, R.T. 1974. Sex pheromones in the reproductive isolation of lepidopterous species,in Pheromones, M.C. Birch, (ed.). p. 96. Elsevier, New York.

    Google Scholar 

  • Rylander, P.N. 1967. Catalytic Hydrogenation over Platinum Metals. Academic Press, New York.

    Google Scholar 

  • Silverstein, R.M., andYoung, J.C. 1976. Pest management with insect sex attractants, p. 1,in M. Beroza (ed.). A.C.S. Symposium Series, No. 23. American Chemical Society, Washington, D.C.

    Google Scholar 

  • Warthen, D. 1968. Synthesis ofcis-9-tetradecen-1-ol acetate, the sex pheromone of the fall armyworm.J. Med. Chem. 11:371–373.

    PubMed  Google Scholar 

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NRCC No. 16834.

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Chisholm, M.D., Steck, W.F. & Underhill, E.W. Geometrical and positional isomerization of alkenyl acetates produced by hydrogenation of alkynyl acetates over palladium metal catalysts. J Chem Ecol 4, 657–663 (1978). https://doi.org/10.1007/BF00990276

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  • DOI: https://doi.org/10.1007/BF00990276

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