Skip to main content
Log in

Mechanism of cycloalkylation of allylcarbinols with aldehydes and ketones

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The reaction of methallylcarbinols with aldehydes and ketones in the presence of acidic catalysts, which leads to mixtures of dihydropyrans and tetrahydropyranols, was studied. It is shown that the formation of tetrahydropyranols occurs as a result of intramolecular bonding of the hydroxy group in the intermediate hemiacetal formed under the influence of the catalyst.

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

Access this article

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. E. Hanschke, Berichte, 88, 1053 (1953).

    Google Scholar 

  2. P. I. Kazaryan, A. A. Gevorkyan, and Sh. O. Badanyan, Arm. Khim. Zh., No. 27, 35 (1974).

    Google Scholar 

  3. P. W. Williams, I. I. Eeke, and S. A. Ballard, J. Am. Chem. Soc., 72, 5738 (1950).

    Google Scholar 

  4. A. A. Gevorkyan, and A. S. Arakelyan, Arm. Khim. Zh., No. 29, 1033 (1976).

    Google Scholar 

  5. A. A. Gevorkyan, and G. G. Tokmadzhan, Arm. Khim. Zh., No. 30, 165 (1977).

    Google Scholar 

  6. A. A. Gevorkyan, V. M. Frosin, and A. S. Arakelyan, USSR Inventor's Certificate No. 505643; Byull. Izobret., No. 9, 65 (1976).

  7. A. A. Gevorkyan, A. S. Arakelyan, N. M. Khizantsyan, G. G. Filotova, V. R. Zanan'yants, and Yu. M. Blazhin, USSR Inventor's Certificate No. 618375; Byull. Izobret., No. 29, 73 (1978).

  8. A. A. Gevorkyan, P. I. Kazaryan, G. G. Filatova, and V. R. Zanan'yants, USSR Inventor's Certificate No. 618374; Byull. Izobret., No. 29, 73 (1978).

  9. D. R. Adams and S. P. Brathagar, Synthesis, 661 (1977).

  10. A. A. Gevorkyan, P. I. Kazaryan, and S. R. Mkrtchyan, Arm. Khim. Zh., No. 28, 508 (1975).

    Google Scholar 

  11. A. S. Arakelyan, Master's Dissertation, Institute of Organic Chemistry, Academy of Sciences of the Armenian SSR, Erevan (1978).

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1611–1613, December, 1982.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Gevorkyan, A.A., Arakelyan, A.S. & Kazaryan, P.I. Mechanism of cycloalkylation of allylcarbinols with aldehydes and ketones. Chem Heterocycl Compd 18, 1240–1242 (1982). https://doi.org/10.1007/BF00506606

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00506606

Keywords

Navigation