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Organoboron compounds. 357. The reaction of (1-isopropyl-o-carboran-2-yl)di-n-butylborane with aldehydes

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

Conclusions

  1. 1.

    We have examined the reactions of (1-isopropyl-o-carboran-2-yl)di-n-butylborane (I) with aliphatic aldehyde and benzaldehyde. With an equimolar reactant ratio, reduction of the aldehyde takes place on heating (50–100°C) and is accompanied by the elimination of 1-butene and the formation of (1-isopropyl-o-carboran-2-yl)-n-butylborinate esters (II).

  2. 2.

    Esters (II) when heated with an equimolar quantity of an aliphatic aldehyde undergo protolysis at the B-C(carborane) bond to form 1-isopropyl-o-carborane.

  3. 3.

    In the presence of hexametapol or pyridine borane (I) reacts with benzaldehyde as an organometallic reagent with cleavage of the B-C(carborane) bond.

  4. 4.

    Borane (I) reacts with aliphatic aldehydes in hexametapol at room temperature, undergoing protolysis at the B-C(carborane) bond.

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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

    B. M. Mikhailov & É. A. Shagova

Authors
  1. B. M. Mikhailov
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  2. É. A. Shagova
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 3, pp. 595–598, March, 1979.

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Mikhailov, B.M., Shagova, É.A. Organoboron compounds. 357. The reaction of (1-isopropyl-o-carboran-2-yl)di-n-butylborane with aldehydes. Russ Chem Bull 28, 549–552 (1979). https://doi.org/10.1007/BF00924830

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  • DOI: https://doi.org/10.1007/BF00924830

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