Elsevier

Tetrahedron

Volume 24, Issue 15, 1968, Pages 5361-5368
Tetrahedron

Hydride transfer reactions of the adamantyl cation—I : A new and convenient synthesis of adamantanone

https://doi.org/10.1016/S0040-4020(01)96329-XGet rights and content

Abstract

Adamantanone can be synthesized from 1-hydroxyadamantane or from adamantane in good yields by treatment with concentrated sulphuric acid. The formation of the ketone is due to disproportionation and oxidation reactions. 2-Hydroxyadamantane—considered to be an intermediate—proved to be formed by a 1,2-hydride shift of the 1-adamantyl cation. Sulphuric acid oxidation of adamantane leading to 1-hydroxyadamantane, followed by a peculiar further sulphuric acid oxidation of 1-hydroxyadamantane, probably via 2-hydroxyadamantane, to adamantanone is reported.

References (19)

  • H.W. Geluk et al.

    Chem. Comm.

    (1967)
  • Chem. Abstr.

    (1967)
  • A.C. Udding et al.

    Chem. Comm.

    (1966)
  • P. von R. Schleyer et al.

    J. Am. Chem. Soc.

    (1961)
  • H. Stetter et al.

    Liebigs Ann.

    (1962)
  • R.C. Fort et al.

    Chem. Rev.

    (1964)
  • G.W. Smith et al.

    J. Org. Chem.

    (1961)
  • E. Müller et al.

    Chem. Ber.

    (1965)
  • S. Landa et al.

    Coll. Czech. Chem. Comm.

    (1967)
There are more references available in the full text version of this article.

Cited by (0)

View full text