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cis-Hydroxylation of 3-methyl-3-norcarene

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

Conclusions

  1. 1.

    The oxidation of 3-methy1-3-norcarene (I) with KMnO4, gives the α- and β-cis-3,4-dihydroxy-3-methylnorcaranes in a 1∶3 ratio, which indicates that the double bond of the starting compound is preferentially attacked from the cis side with respect to the cyclopropane ring.

  2. 2.

    The hydroxylation of (I) with Hg2(OAc)2-I2-AcOH-H2O gave β-cis-3,4-dihydroxy-3-methyl-norcarane.

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Authors and Affiliations

  1. A. E. Arbuzbv Institute of Organic and Physical Chemistry, Kazan Branch of the Academy of Sciences of the USSR, USSR

    É. Kh. Kazakova & S. V. Filippova

Authors
  1. É. Kh. Kazakova
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  2. S. V. Filippova
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 12, pp. 2781–2784, December, 1980.

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Kazakova, É.K., Filippova, S.V. cis-Hydroxylation of 3-methyl-3-norcarene. Russ Chem Bull 29, 1952–1955 (1980). https://doi.org/10.1007/BF00949664

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  • DOI: https://doi.org/10.1007/BF00949664

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