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Stereoselectivity of hydroboration of 3-methylbicyclo[4.1.0]-2-heptene

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

Conclusions

  1. 1.

    The oxidative hydroboration of 3-methylbicyclo[4.1.0]-2-heptene proceeds stereoseleetively to give cls-3-methylbicyclo[4.1.0]heptan-trans-2-ol.

  2. 2.

    The hydrogenolysis of cis-3-methylbicyclo[4.1.0]-2-heptanone gives cis-3-methylbicyclo[4.1.0]heptantrans-2-ol; the hydrogenolysis of trans-3-methylbicyclo[4.1.0]-2-heptanone leads to the formation of the alcohols trans-3-mettoylbicyclo[4.1.0]heptan-cis-2-ol and trans-3-methylbicyclo[4.1.0]heptan-trans-2-ol in a. 1.2∶1 ratio.

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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 4, pp. 875–878, April 1980.

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Kazakova, E.K., Surkova, L.N. & Bikeev, S.S. Stereoselectivity of hydroboration of 3-methylbicyclo[4.1.0]-2-heptene. Russ Chem Bull 29, 625–628 (1980). https://doi.org/10.1007/BF00961617

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  • DOI: https://doi.org/10.1007/BF00961617

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