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Synthesis of 1,4,5-trimethyl-7-thiabicyclo[2.2.2]octan-2-one from 3,7-dimethyl-5-thianonan-2,8-dione

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Abstract

It was found that the heating of 3,7-dimethyl-5-thianonan-2,8-dione at 50°C in ethanol in the presence of potassium hydroxide yields 1,4,5-trimethyl-7-thiabicyclo[2.2.2]octan-2-one as a mixture of 5-exo-and 5-endo-isomers in the ratio of 5:1. The oxidation of thiabicyclooctanone with hydrogen peroxide and its reduction with sodium borohydride result in 1,4,5-trimethyl-7-thiabicyclo[2.2.2]octane-2-one-7,7-dioxide and 1,4,5-trimethyl-7-thiabicyclo[2.2.2]octane-2-ol, respectively.

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Authors and Affiliations

  1. Institute of Organic Chemistry, Ufa Scientific Center, Russian Academy of Sciences, pr. Oktyabrya 71, Ufa, 450054, Bashkortostan, Russia

    L. A. Baeva, A. D. Ulendeeva, A. R. Gaisina, O. V. Shitikova, E. G. Galkin & N. K. Lyapina

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  1. L. A. Baeva
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  2. A. D. Ulendeeva
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  3. A. R. Gaisina
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  4. O. V. Shitikova
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  5. E. G. Galkin
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  6. N. K. Lyapina
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Original Russian Text © L.A. Baeva, A.D. Ulendeeva, A.R. Gaisina, O.V. Shitikova, E.G. Galkin, N.K. Lyapina, 2007, published in Neftekhimiya, 2007, Vol. 47, No. 2, pp. 134–138.

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Baeva, L.A., Ulendeeva, A.D., Gaisina, A.R. et al. Synthesis of 1,4,5-trimethyl-7-thiabicyclo[2.2.2]octan-2-one from 3,7-dimethyl-5-thianonan-2,8-dione. Pet. Chem. 47, 118–122 (2007). https://doi.org/10.1134/S0965544107020090

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  • DOI: https://doi.org/10.1134/S0965544107020090

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