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Reduction of unsaturated ketones by 2-propanol, catalyzed by the complexes RhCl(PPh3)3 and RuCl2(PPh3)3

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

Conclusions

  1. 1.

    Triphenylphosphine complexes of rhodium (I) and ruthenium (II) catalyze reduction ofα,β-unsaturated ketones with hydrogen transfer from 2-propanol consecutively: the C=C bond is saturated initially, and then the C=0 group.

  2. 2.

    In the presence of complexes of rhodium 3,5-dimethyl-2-cyclohexenone and 3,5-dimethyl-3-cyclohexenone are reduced with 2-propanol stereoselectively with predominate formation of the thermodynamically less stable form (eea) of cis-3,5-dimethylcyclohexanol; in the presence of RuCl2(PPh3)3 the thermodynamically more stable form (eee) is formed.

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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

    V. Z. Sharf, L. Kh. Freidlin, I. S. Shekoyan & V. N. Krutii

Authors
  1. V. Z. Sharf
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  2. L. Kh. Freidlin
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  3. I. S. Shekoyan
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  4. V. N. Krutii
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Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 4, pp. 834–837, April, 1977.

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Sharf, V.Z., Freidlin, L.K., Shekoyan, I.S. et al. Reduction of unsaturated ketones by 2-propanol, catalyzed by the complexes RhCl(PPh3)3 and RuCl2(PPh3)3 . Russ Chem Bull 26, 758–762 (1977). https://doi.org/10.1007/BF01108195

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  • DOI: https://doi.org/10.1007/BF01108195

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