Skip to main content
SpringerLink
Log in

Acyl Iodides in Organic Synthesis: VI. Reactions with Vinyl Ethers

  • Published:
Russian Journal of Organic Chemistry Aims and scope Submit manuscript

Abstract

Reactions of acetyl iodide with butyl vinyl ether, 1,2-divinyloxyethane, phenyl vinyl ether, 1,4-di-vinyloxybenzene, and divinyl ether were studied. Vinyl ethers derived from aliphatic alcohols (butyl vinyl ether and 1,2-divinyloxyethane) react with acetyl iodide in a way similar to ethyl vinyl ether, i.e., with cleavage of both O–Csp2 and Alk–O ether bonds. From butyl vinyl ether, a mixture of vinyl iodide, butyl acetate, vinyl acetate, and butyl iodide is formed, while 1,2-divinyloxyethane gives rise to vinyl iodide, vinyl acetate, and 2-iodoethyl acetate. The reaction of acetyl iodide with divinyl ether involves cleavage of only one O–Csp2 bond, yielding vinyl acetate and vinyl iodide. In the reactions of acetyl iodide with phenyl vinyl ether and 1,4-divinyloxybenzene, only the O–CVin bond is cleaved, whereas the O–CAr bond remains intact.

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

REFERENCES

  1. Voronkov, M.G., Trukhina, A.A., and Vlasova, N.N., Russ. J. Org. Chem., 2004, vol. 40, p. 357.

    Google Scholar 

  2. Voronkov, M.G., Trukhina, A.A., and Vlasova, N.N., Russ. J. Org. Chem., 2002, vol. 38, p. 1579.

    Google Scholar 

  3. Shostakovskii, M.F., Prostye vinilovye efiry (Vinyl Ethers), Moscow: Akad. Nauk SSSR, 1952, p. 55.

    Google Scholar 

  4. Trofimov, B.A., Emel'yanov, I.S., Yasel'man, M.E., and Atavin, A.S., Reakts. Sposobn. Org. Soedin., 1969, vol. 6, p. 934.

    Google Scholar 

  5. Andersson, K.-M. and Hallberg, A., Tetrahedron Lett., 1987, vol. 28, p. 4215.

    Google Scholar 

  6. Basenko, S.V., Boyarkina, E.V., and Voronkov, M.G., Russ. J. Gen. Chem., 2003, vol. 73, p. 488.

    Google Scholar 

  7. Iqbal, J. and Strivastava, R.R., Tetrahedron, 1991, vol. 47, p. 3155.

    Google Scholar 

  8. Stevens, Ph.G., J. Am. Chem. Soc., 1934, vol. 56, p. 450.

    Google Scholar 

  9. Voronkov, M.G., Zh. Fiz. Khim., 1947, vol. 21, p. 969.

    Google Scholar 

  10. Shagun, V.A. and Voronkov, M.G., Russ. J. Org.Chem., 2003, vol. 39, p. 331.

    Google Scholar 

  11. Gustes, E.L. and Stevens, Ph.G., J. Am. Chem. Soc., 1933, vol. 55, p. 378.

    Google Scholar 

  12. Svoistva organicheskikh soedinenii. Spravochnik (Properties of Organic Compounds. Handbook), Potekhin, A.A., Ed., Leningrad: Khimiya, 1984.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Favorskii Irkutsk Institute of Chemistry, Siberian Division, Russian Academy of Sciences, ul. Favorskogo 1, Irkutsk, 664033, Russia

    M. G. Voronkov, A. A. Trukhina & N. N. Vlasova

Authors
  1. M. G. Voronkov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. A. A. Trukhina
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. N. N. Vlasova
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

About this article

Cite this article

Voronkov, M.G., Trukhina, A.A. & Vlasova, N.N. Acyl Iodides in Organic Synthesis: VI. Reactions with Vinyl Ethers. Russian Journal of Organic Chemistry 40, 467–469 (2004). https://doi.org/10.1023/B:RUJO.0000036063.58577.17

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1023/B:RUJO.0000036063.58577.17

Keywords

Search

Navigation