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Organoboron compounds 356. The protolysis of (1-isopropyl-o-carboranyl-2)-di-n-butylborane

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

Conclusions

  1. 1.

    (1-Isopropyl-o-carboranyl-2)-di-n-butylborane (I) is cleaved at the B-C4H9 bond by the action of acetic acid, while methanol, BuSH, and amines, depending on the nature of the reagent and the reaction conditions, may cleave the B-C4H9 or B-C carborane bond or both these bonds.

  2. 2.

    Under conditions of nucleophilic catalysis as a result of the coordination of Lewis bases (amines, alcohols, and THF) with the boron atom in the side-chain, the protolytic cleavage of (I) by an alcohol or mercaptan proceeds at the B-C carborane bond.

  3. 3.

    Electrophilic substitution, in which the reagent initially forms a coordination compound with the reacting molecule and then the complex reacts by a bimolecular mechanism, should be represented by the symbol SEC2.

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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 & V. G. Kiselev

Authors
  1. B. M. Mikhailov
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  2. É. A. Shagova
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  3. V. G. Kiselev
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Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 3, pp. 589–594, March, 1979.

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Mikhailov, B.M., Shagova, É.A. & Kiselev, V.G. Organoboron compounds 356. The protolysis of (1-isopropyl-o-carboranyl-2)-di-n-butylborane. Russ Chem Bull 28, 543–548 (1979). https://doi.org/10.1007/BF00924829

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  • DOI: https://doi.org/10.1007/BF00924829

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