Skip to main content
SpringerLink
Log in

Reactions of bisdiazonium salts derived from monosubstituted m-phenylenediamines with amides and nitriles of unsaturated acids under anionarylation conditions

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

Abstract

Reactions of 5-carboxy and 4-methylphenylene-1,3-bisdiazonium tetrafluoroborates with amides and nitriles of acrylic and methacrylic acids in the presence of chloride, bromide, and thiocyanate anions proceed as anionarylation at one of the diazo groups and nucleophilic substitution at another one. With 4-methylphenylene- 1,3-bisdiazonium tetrafluoroborate as the arylating agent, the anionarylation and the Sandmeyer reaction occur involving para- and ortho-positioned diazo groups, respectively.

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. Obushak, N.D., Ganushchak, N.I., Lesyuk, A.I., Pil’o, S.G., Demchuk, O.M., and Mazyar, L.P., Zh. Org. Khim., 1997, Vol. 33, No. 4, p. 490.

    Google Scholar 

  2. Baranovskii, V.S., Yatsyuk, V.N., and Grishchuk, B.D., Russ. J. Gen. Chem., 2014, Vol. 88, No. 8, p. 1505. DOI: 10.1134/S1070363214080106.

    Article  Google Scholar 

  3. Dombrovskii, A.V., Russ. Chem. Rev., 1984, Vol. 53, No. 10, p. 943.

    Article  Google Scholar 

  4. Grishchuk, B.D., Gorbovoi, P.M., Ganushchak, N.I., and Dombrovskii, A.V., Russ. Chem. Rev., 1994, Vol. 63, No. 3, p. 257.

    Article  Google Scholar 

  5. Grishchuk, B.D., Gorbovii, P.M., Baranovskii, V.S., and Ganushchak, M.I., Zh. Org. Farm. Khim., 2008, Vol. 6, No. 3(23), p. 16.

    CAS  Google Scholar 

  6. Yatsyuk, V.M., Tulaidan, G.M., Baranovskii, V.S., and Grishchuk, B.D., Book of Abstracts, ХХІІІ Ukrainskaya konferentsiya po organicheskoi khimii (XXIII Ukrainian Conference on Organic Chemistry), Chernovtsy, 2013, p. C–17.

    Google Scholar 

  7. Stempel, G.H., Greene, Ch., Rongone, R., Sobel, B., and Odioso, R., J. Am. Chem. Soc., 1951, Vol. 73, No. 1, p. 455.

    Article  CAS  Google Scholar 

  8. Bogert, M.T. and Hand, W.F., J. Chem. Soc., 1903, Vol. 25, p. 942.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Hnatiuk Ternopil National Pedagogical University, ul. M. Kryvonosa 2, Ternopil, 46027, Ukraine

    V. S. Baranovskii, V. N. Yatsyuk & B. D. Grishchuk

  2. Institute of Bioorganic Chemistry and Petrochemistry, National Academy of Sciences of Ukraine, Kiev, Ukraine

    A. N. Vasilenko

Authors
  1. V. S. Baranovskii
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. V. N. Yatsyuk
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. A. N. Vasilenko
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. B. D. Grishchuk
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to V. S. Baranovskii.

Additional information

Original Russian Text © V.S. Baranovskii, V.N. Yatsyuk, A.N. Vasilenko, B.D. Grishchuk, 2015, published in Zhurnal Obshchei Khimii, 2015, Vol. 85, No. 8, pp. 1262–1266.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Baranovskii, V.S., Yatsyuk, V.N., Vasilenko, A.N. et al. Reactions of bisdiazonium salts derived from monosubstituted m-phenylenediamines with amides and nitriles of unsaturated acids under anionarylation conditions. Russ J Gen Chem 85, 1821–1825 (2015). https://doi.org/10.1134/S1070363215080058

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070363215080058

Keywords

Search

Navigation