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Oxidative addition of acetone to butadiene

  • Organic Chemistry
  • Published:
Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Conclusions

  1. 1.

    Oxidative addition of acetone to butadiene in the presence of the system Mn(OAc)3-Cu(OAc)2 has afforded 5-acetoxy-6-hepten-2-one, three isomeric 1-methyl-3,7-divinyl-2,8-dioxa-cis-bicyclo[3.3.0]octanes with the vinyl groups with the exo,exo, exo,endo, and endo,endo dispositions, and three diastereoisomeric 2,7-divinyl-1,6-dioxaspiro[4.4]nonanes.

  2. 2.

    Oxidative addition of acetopropyl alcohol and dihydrosylvan to butadiene results in the formation in both cases of identical mixtures of exo- and endo-1-methyl-3-vinyl-2,8-dioxa-cis-bicyclo[3.3.0]octanes and diastereoisomeric 2-vinyl-1,6-dioxaspiro[4.4]nonanes, indicating that the reaction proceeds via the same intermediate, probably a complex of Mn(III) with the ketoalcohol.

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Literature cited

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Authors and Affiliations

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

    M. G. Vinogradov, M. S. Pogosyan, A. Ya. Shteinshneider & G. I. Nikishin

Authors
  1. M. G. Vinogradov
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  2. M. S. Pogosyan
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  3. A. Ya. Shteinshneider
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  4. G. I. Nikishin
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Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 4, pp. 842–847, April, 1983.

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Vinogradov, M.G., Pogosyan, M.S., Shteinshneider, A.Y. et al. Oxidative addition of acetone to butadiene. Russ Chem Bull 32, 768–772 (1983). https://doi.org/10.1007/BF00953473

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  • DOI: https://doi.org/10.1007/BF00953473

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