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Organoboron compounds. 370. Allylboron-acetylene condensation by the use of tricrotylborane and the synthesis of 4,6-dimethyl-1-boraadamantane

  • B. M. Mikhailov
  • M. E. Gurskii
  • A. S. Shashkov
Organic Chemistry

Conclusions

  1. 1.

    Tricrotylborane reacts with propargyl methyl ether with the formation of derivatives of 7-methoxymethyl-8,9-dimethyl-3-borabicyclo[3.3.1]non-6-ene.

     
  2. 2.

    The second stage of the allylboron-acetylene condensation — formation of 3-substituted 1,5-diallyl-1-boracyclohex-2-enes — proceeds with the allyl regrouping. Stereospecificity of the second stage of the reaction of tricrotylborane with propargyl methyl ether is observed.

     
  3. 3.

    Complexes of 4,6-dimethyl-1-boraadamantane with THF and pyridine are obtained during hydroboronation of 3-methoxy-7-methoxymethyl-8,9-dimethyl-3-borabicyclo[3.3.1]non-6-ene.

     
  4. 4.

    On the basis of13C NMR, one methyl group occupies the axial, and the other the equatorial position in 4,6-dimethyl-1-boraadamantane.

     

Keywords

Methyl Ether Pyridine Allyl Methyl Ether 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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Copyright information

© Plenum Publishing Corporation 1980

Authors and Affiliations

  • B. M. Mikhailov
    • 1
  • M. E. Gurskii
    • 1
  • A. S. Shashkov
    • 1
  1. 1.N. D. Zelinskii Institute of Organic ChemistryAcademy of Sciences of the USSRMoscow

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