Skip to main content
SpringerLink
Log in

Mono- and Di(dechloromethylthioylation) of Dichloromethylarenes with S-Methyl Diethylthiophosphinate

  • CHEMISTRY
  • Published:
Doklady Chemistry Aims and scope Submit manuscript

Abstract

The attack of the thiol sulfur atom (P–SMe) on the methine carbon as the main route of the new reaction of dichloromethylarenes with S-methyl diethylthiophosphinate has been predicted and experimentally confirmed on the basis of the electronic structure of the S-alkyl esters of P(IV) acids. The processes of the mono- and di(dechloromethylthioylation) of dichloromethyl group have been realized. A new approach to the synthesis of the arenecarbaldehyde dimethyl dithioacetals has been developed avoiding the use of gaseous highly toxic methyl mercaptan.

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. Gazizov, M.B., Kachalova, T.N., Karimova, R.F., Khairullin, R.A., and Sinyashin, O.G., Zh. Obshch. Khim., 1997, vol. 67, no. 12, pp. 2055–2056.

    Google Scholar 

  2. Gazizov, M.B., Kachalova, T.N., Karimova, R.F., Khairullin, R.A., and Sinyashin, O.G., Dokl. Akad. Nauk, 1998, vol. 359, no. 15, pp. 644–645.

    CAS  Google Scholar 

  3. Zverev, V.V. and Villem, Ya.Ya., Zh. Strukt. Khim., 1980, vol. 21, no. 1, pp. 30–34.

    CAS  Google Scholar 

  4. Ranu, B.C., Saha, A., and Mandal, T., Tetrahedron, 2009, vol. 65, no. 10, pp. 2072–2078.

    Article  Google Scholar 

  5. Cragg, R.H. and Husband, J.P.N., Inorg. Nucl. Chem. Lett., 1970, vol. 6, no. 9, pp. 773–774.

    Article  Google Scholar 

  6. Pourshahbaz, M., Joshaghani, M., Rafiee, E., Shahmoradi, J., Emami, F., and Iranpour, A., Tetrahedron Lett., 2009, vol. 50, no. 44, pр. 5987–5989.

  7. Drosten, G., Mischke, P., and Voß, J., Chem. Ber., 1987, vol. 120, no. 10, pp. 1757–1761.

    Article  Google Scholar 

  8. Alonso, G., Alvarez-Ibarra, C., Orellana, G., and Quiroga, M.L., Bull. Soc. Chim. Belg., 1989, vol. 98, no. 3, pp. 215–220.

    Article  CAS  Google Scholar 

Download references

Funding

This work was supported by the Ministry of Education and Science of the Russian Federation (State assignment nos. 4.5348.2017/8.9 and 4.5151.2017/6.7).

Author information

Authors and Affiliations

  1. Kazan State Technological University, 420015, Kazan, Russia

    M. B. Gazizov, G. D. Valieva, S. Yu. Ivanova, R. A. Khairullin & Yu. S. Kirillina

  2. Kazan State University, 420008, Kazan, Russia

    I. S. Antipin

Authors
  1. M. B. Gazizov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. G. D. Valieva
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. S. Yu. Ivanova
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. R. A. Khairullin
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Yu. S. Kirillina
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. I. S. Antipin
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to M. B. Gazizov.

Additional information

Translated by I. Kudryavtsev

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Gazizov, M.B., Valieva, G.D., Ivanova, S.Y. et al. Mono- and Di(dechloromethylthioylation) of Dichloromethylarenes with S-Methyl Diethylthiophosphinate. Dokl Chem 489, 257–260 (2019). https://doi.org/10.1134/S0012500819110016

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S0012500819110016

Search

Navigation