Skip to main content
SpringerLink
Log in

Nucleophilic addition of nitriles to tertiary monocyclic terpenes alcohols

  • Published:
Chemistry of Natural Compounds Aims and scope

Abstract

Previously unknown secondary amines have been synthesized by the Ritter reaction of p-menthan-8-ol with propio- and benzonitriles. The performance of this reaction with α-terpeneol and benzonitrile led to the formation of a mixture of N-(p-menth-1-en-8-yl)benzamide and N,N-(p-menth-1,8-diyl)dibenzamide. A transdiamide was also obtained on the reaction of α-terpineol with isovaleronitrile. The use of propionitrile as the nucleophile with α-terpineol led to the formation of 2-ethyl-4,4,8-trimethyl-8-propionamido-3-azabicyclo[3.3.1]non-2-ene.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

Literature cited

  1. N. K. Kochetkov, A. Ya. Khorlin, and K. I. Lopatina, Zh. Obshch. Khim., No. 1, 75 (1959).

  2. N. G. Kozlov, L. A. Popova, and M. G. Novikova, Zh. Org. Khim., No. 3, 536 (1986).

  3. FRG Patent No. 3136580 (1983); Chem. Abstr.,99, 54021 (1983).

    Google Scholar 

  4. J. Caram, M. E. Martins, C. M. Marschroft, L. F. R. Cafferata, and E. J. Gross, Naturforsch.,39B, 972 (1984).

    Google Scholar 

  5. R. B. Chikh, R. Chaabouni, A. Laurent, P. Mison, and O. Nafti, Synthesis,9, 685 (1983).

    Google Scholar 

  6. V. M. Potapov, Stereochemistry [in Russian], Khimiya, Moscow (1976), p. 344.

    Google Scholar 

  7. V. I. Lysenkov, T. I. Pekhk, and G. N. Bazhina, Izv. Akad. Nauk BSSR, Ser. Khim., No. 1, 60 (1985).

  8. J. J. Ritter and P. P. Minieri, J. Am. Chem. Soc.,70, No. 5, 4045 (1948).

    Google Scholar 

Download references

Authors
  1. L. A. Popova
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. N. G. Kozlov
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

Institute of Physical Organic Chemistry, Academy of Sciences of the Belorussian SSR, Minsk. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 235–240, March–April, 1987.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Popova, L.A., Kozlov, N.G. Nucleophilic addition of nitriles to tertiary monocyclic terpenes alcohols. Chem Nat Compd 23, 196–200 (1987). https://doi.org/10.1007/BF00598756

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00598756

Keywords

Search

Navigation