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Reduction of α-epoxides with hydrodiisobutylaluminum and the mechanism of the action of simple aluminum hydrides on α-epoxides

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

Summary

  1. 1.

    The hydrogenolysis of α-epoxides with the aid of hydrodiisobutylaluminum was studied. The action of hydrodiisobutylaluminum differs from that of lithium aluminum hydride and is similar to that of simple aluminum hydrides such as AlH3, AlH2Cl, and AlHCl2.

  2. 2.

    The peculiar feature of hydrodiisobutylaluminum and simple aluminum hydrides as reducing agents lies in the power to coordinate electron-donor molecules. A mechanism for the reduction of α-epoxides with simple aluminum hydrides is proposed.

  3. 3.

    Unlike Rerick and Eliel [4], we found that in the reduction of 2,3-epoxy-2,4,4-trimethylpentane with 1∶1 and 3∶1 mixtures of LiAlH4 and AlCl3,2,4,4-trimethyl-2-pentanol is formed in addition to 2,2,4-trimethyl-3-pentanol, 2,4,4-tiimethyl-1-penten-3-ol, and 2,2,3,3-tetramethyl-1-butanol.

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Authors and Affiliations

  1. Institute of Heteroorganic Compounds, Academy of Sciences, USSR

    L. I. Zakharkin & I. M. Khorlina

Authors
  1. L. I. Zakharkin
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  2. I. M. Khorlina
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 5, pp. 862–870, May, 1965 Original article submitted May 9, 1963

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Zakharkin, L.I., Khorlina, I.M. Reduction of α-epoxides with hydrodiisobutylaluminum and the mechanism of the action of simple aluminum hydrides on α-epoxides. Russ Chem Bull 14, 834–839 (1965). https://doi.org/10.1007/BF00845698

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  • DOI: https://doi.org/10.1007/BF00845698

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