Skip to main content
Log in

Reaction of tetra(phenylethynyl)tin with aromatic aldehydes: A new one-pot method for the synthesis of α-acetylene ketones

  • Letters to the Editor
  • Published:
Russian Journal of General Chemistry Aims and scope Submit manuscript

Abstract

The reaction of tetra(phenylethynyl)tin with aromatic aldehydes in the presence of ZnCl2 afforded α-acetylene ketones in a yield of 77–98%.

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.

References

  1. Zou, J., Zeng, G., Yang, R., and Yin, B., Synthesis, 2017, vol. 49, p. 1. doi 10.1055/s-0036-1588717

    Google Scholar 

  2. Schmidt, B., Riemer, M., and Schilde, U., Eur. J. Org. Chem., 2015, vol. 2015, p. 7602. doi 10.1002/ejoc.201501151

    Article  CAS  Google Scholar 

  3. Jonušis, M., Šteinys, L., Bukšnaitiene, R., and Cikotiene, I., Synthesis, 2016, vol. 48, p. 1. doi 10.1055/s-0036-1588327

    Google Scholar 

  4. Song, Y.-K., Qian, P.-C., Chen, F., Deng, C.-L., and Zhang, X.-G., Tetrahedron, 2016, vol. 72, p. 7589. doi 10.1016/j.tet.2016.10.013

    Article  CAS  Google Scholar 

  5. Shao, J., Huang, X., Hong, X., Liu, B., and Xu, B., Synthesis, 2012, vol. 44, no. 12, p. 1798. doi 10.1055/s-0031-1290775

    Article  CAS  Google Scholar 

  6. Yin, L. and Wang, L., Tetrahedron Lett., 2016, vol. 57, no. 52, p. 5935. doi 10.1016/j.tetlet.2016.11.089

    Article  CAS  Google Scholar 

  7. Clarke, A.K., James, M.J., Brien, P.O., Taylor, R.J.K., and Unsworth, W.P., Angew. Chem. Int. Ed., 2016, vol. 55, p. 13798. doi 10.1002/anie.201608263

    Article  CAS  Google Scholar 

  8. Livingston, R., Cox, L.R., Odermatt, S., and Diederich, F., Helv. Chim. Acta, 2002, vol. 85, no. 10, p. 3052. doi 10.1002/1522-2675(200210)85:10<3052::AID-HLCA3052> 3.0.CO;2-4

    Article  CAS  Google Scholar 

  9. Müller, V.E., Beißner, C., Jäkle, H., Langer, E., Muhm, H., Odenigbo, G., Sauerbier, M., Segnitz, A., Streichfuß, D., and Thomas, R., Lieb. Ann. Chem., 1972, vol. 754, p. 64. doi 10.1002/jlac. 19717540109

    Article  Google Scholar 

  10. Jong, T.-T. and Leu, S.-J., J. Chem. Soc., Perkin Trans. 1, 1990, no. 2, p. 423. doi 10.1039/P19900000423

    Article  Google Scholar 

  11. Ushijima, S., Dohi, S., Moriyama, K., and Togo, H., Tetrahedron, 2012, vol. 68, no. 5, p. 1436. doi 10.1016/j.tet.2011.12.023

    Article  CAS  Google Scholar 

  12. Suzuki, I., Esumi, N., Yasuda, M., and Baba, A., Chem. Lett., 2015, vol. 44, no. 1, p. 38. doi 10.1246/cl.140888

    Article  Google Scholar 

  13. Okabe, T., Kuzuhara, D., Suzuki, M., Aratani, N., and Yamada, H., Org. Lett., 2014, vol. 16, no. 13, p. 3508. doi 10.1021/ol5014608

    Article  CAS  Google Scholar 

  14. Levashov, A.S., Andreev, A.A., and Konshin, V.V., Tetrahedron Lett., 2015, vol. 56, no. 14, p. 1870. doi 10.1016/j.tetlet.2015.02.095

    Article  CAS  Google Scholar 

  15. RF Patent 2317993, 2006; Byull. Izobret., 2008, no. 6.

  16. Levashov, A.S., Andreev, A.A., Buryi, D.S., and Konshin, V.V., Russ. Chem. Bull., 2014, vol. 63, p. 775. doi 10.1007/s11172-014-0508-8

    Article  CAS  Google Scholar 

  17. Jaumier, P., Jousseaume, B., and Lahcini, M., Angew. Chem. Int. Ed., 1999, vol. 38, p. 402. doi 10.1002/(SICI)1521-3773(19990201)38:3<402::AID-ANIE402> 3.0.CO;2-C

    Article  CAS  Google Scholar 

  18. Wrackmeyer, B. and Kehr, G., J. Organomet. Chem., 1995, vol. 501, nos. 1–2, p. 87. doi 10.1016/0022-328X (95)05619-Z

    Article  CAS  Google Scholar 

  19. Levashov, A.S., Buryi, D.S., Goncharova, O.V., Konshin, V.V., Dotsenko, V.V., and Andreev, A.A., New J. Chem., 2017, vol. 41, p. 2910. doi 10.1039/C6NJ03905G

    Article  CAS  Google Scholar 

  20. Ogiwara, Y., Kubota, M., Kurogi, K., Konakahara, T., and Sakai, N., Chem. Eur. J., 2015, vol. 21, no. 51, p. 18598. doi 10.1002/chem.201504255

    Article  CAS  Google Scholar 

  21. Dolomanov, O.V., Bourhis, L.J., Gildea, R.J., Howard, J.A.K., and Puschmann, H., J. Appl. Crystallogr., 2009, vol. 42, p. 339. doi 10.1107/S0021889808042726

    Article  CAS  Google Scholar 

  22. Sheldrick, G.M., Acta Crystallogr., 2015, vol. 71, p. 3. doi 10.1107/S2053229614024218

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to A. S. Levashov.

Additional information

Original Russian Text © A.S. Levashov, D.S. Buryi, V.V. Konshin, V.V. Dotsenko, N.A. Aksenov, I.V. Aksenova, 2017, published in Zhurnal Obshchei Khimii, 2017, Vol. 87, No. 7, pp. 1200–1203.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Levashov, A.S., Buryi, D.S., Konshin, V.V. et al. Reaction of tetra(phenylethynyl)tin with aromatic aldehydes: A new one-pot method for the synthesis of α-acetylene ketones. Russ J Gen Chem 87, 1627–1630 (2017). https://doi.org/10.1134/S1070363217070295

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070363217070295

Keywords

Navigation