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Reactions of carboxylic acids and their derivatives with compounds of variable valence metals

Communication 1. Dehydrocarboxylation of acetoxyalkanoic acids

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Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Conclusions

  1. 1.

    A study was made of the dehydrocarboxylation of some acetoxyalkanoic acids RR'CHCH(COOH) (CH2)nOAc by the joint action of the tetravalent lead and divalent copper acetates in the presence of pyridine.

  2. 2.

    Conditions were found for running the dehydrocarboxylation that assured a high conversion of the acids to the cis- and trans-acetates RR'CH=CH(CH2)nOAc and RR'CHCH=CH(CH2)n-1OAc.

  3. 3.

    The mutual arrangement of the acetoxyl and carboxyl groups and the structure of the RR'CH fragment of the acid exert a substantial influence on the ratio of the formed acetates.

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Literature cited

  1. J. D. Bacha and J. K. Kochi, J. Org. Chem.,33, 83 (1968).

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  2. J. D. Bacha and J. K. Kochi, Tetrahedron,24, 2215 (1968).

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  3. G. I. Nikishin, Yu. N. Ogibin, and A. D. Pelrov, Dokl. Akad. Nauk SSSR, 138, 393 (1961).

  4. K. B. Wiberg (editor), Oxidation in Organic Chemistry, Part A, Academic Press, New York (1965). p. 279.

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Authors and Affiliations

  1. N. D. Zelinskii Institute of Organic Chemistry, Academy of Sciences of the USSR, USSR

    Yu. N. Ogibin, M I. Katsin & G. I. Nikishin

Authors
  1. Yu. N. Ogibin
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  2. M I. Katsin
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  3. G. I. Nikishin
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Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 3, pp. 587–592, March, 1973.

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Ogibin, Y.N., Katsin, M.I. & Nikishin, G.I. Reactions of carboxylic acids and their derivatives with compounds of variable valence metals. Russ Chem Bull 22, 562–566 (1973). https://doi.org/10.1007/BF00854025

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  • DOI: https://doi.org/10.1007/BF00854025

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