Skip to main content
Log in

O-Trimethylsilyl-N-phenylsulfonylacetimidate: Synthesis and Structure

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

Abstract

A method for silylation of N-acetylbenzenesulfonamide has been proposed. The structural features of the obtained O-trimethylsilyl-N-phenylsulfonylacetimidate have been studied by means of NMR and IR spectroscopy as well as single-crystal X-ray diffraction analysis.

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.

Scheme
Scheme
Fig. 1.
Fig. 2.

Similar content being viewed by others

REFERENCES

  1. Kashutina, M.V., Ioffe, S.L., and Tartakovskii, V.A., Russ. Chem. Rev., 1975, vol. 44, no. 9, p. 1620. https://doi.org/10.1070/RC1975v044n09ABEH002373

    Article  CAS  Google Scholar 

  2. Mizhiritskii, M.D. and Yuzhelevskii, Yu.A., Russ. Chem. Rev., 1987, vol. 56, no. 4, p. 355. https://doi.org/10.1070/RC1987v056n04ABEH003276

    Article  Google Scholar 

  3. Look, G., Silylating Agents, Buchs: Fluka Chemie AG, 1995.

  4. Auner, N. and Weis, J., Organosilicon Chemistry From Molecules to Materials, Weinheim: VCH, 1994.

  5. Greene, T.W. and Wuts, P.G.M., Protective Groups in Organic Synthesis, New York: John Wiley and Sons, 1999.

  6. Splitter, J.S. and Turecek, F., Applications of Mass Spectrometry to Organic Stereochemistry, Weinheim: VCH, 1994.

  7. Klebe, J.F., Acc. Chem. Res., 1970, vol. 3, no. 9, p. 299. https://doi.org/10.1021/ar50033a003

    Article  CAS  Google Scholar 

  8. Verboom, W., Visser, G.W., and Reinhoudt, D.N., Synthesis, 1981, no. 10, p. 807. https://doi.org/10.1055/s-1981-29605

    Article  Google Scholar 

  9. Gihani, M.T. and Heaney, H., Synthesis, 1998, no. 4, p. 357. https://doi.org/10.1055/s-1998-2043

    Article  Google Scholar 

  10. Shinichi, I. and Iwao, O., J. Organometal. Chem., 1979, vol. 169, no. 2, p. 171. https://doi.org/10.1016/S0022-328X(00)81156-0

    Article  Google Scholar 

  11. Iwao, O., Shinichi, I., and Yoichiro, N., J. Chem. Soc. Chem. Commun., 1974, no. 20, p. 826. https://doi.org/10.1039/c39740000826

    Article  Google Scholar 

  12. Gordetsov, F.S., Vostokov, I.A., Dergunov, Yu.I., and Mushkin, Yu.I., Zh. Obshch. Khim., 1974, vol. 44, no. 11, p. 2456.

    CAS  Google Scholar 

  13. Reddy, C.R., Mahipal, B., and Yaragorla, S.R., Tetrahedron Lett., 2007, vol. 48, no. 42, p. 7528. https://doi.org/10.1016/j.tetlet.2007.08.048

    Article  CAS  Google Scholar 

  14. Deng, H., Han, T., Zhao, E., Kwok, R.T.K., Lam, J.W.Y., and Tang, B.Z., Polym. Chem., 2016, vol. 7, no. 36, p. 5646. https://doi.org/10.1039/C6PY01337F

    Article  CAS  Google Scholar 

  15. Yao, Z.-J., Li, K., Zhang, J.-Y., Wang, Y., and Deng, W., Inorg. Chim. Acta, 2016, vol. 450, p. 118. https://doi.org/10.1016/j.ica.2016.05.032

    Article  CAS  Google Scholar 

  16. Anugu, R.R. and Chegondi, R., J. Org. Chem., 2017, vol. 82, no. 13, p. 6786. https://doi.org/10.1021/acs.joc.7b00936

    Article  CAS  PubMed  Google Scholar 

  17. Peng, J., Cui, H., and Chen, J.C., Sci. China. Chem., 2011, vol. 54, p. 81. https://doi.org/10.1007/s11426-010-4137-2

    Article  CAS  Google Scholar 

  18. Nikolaev, V., Hennig, L., Sieler, J., Rodina, L., Schulze, B., and Nikolaev, B., Org. Biomol. Chem., 2005, vol. 3, no. 22, p. 4108. https://doi.org/10.1039/b508317f

    Article  CAS  PubMed  Google Scholar 

  19. Shen, R. and Huang, X., J. Org. Chem., 2007, vol. 72, no. 10, p. 3961. https://doi.org/10.1021/jo070239z.

    Article  CAS  PubMed  Google Scholar 

  20. Dabbagh, H.A., Modarresi-Alam, A.R., Tadjarodi, A., and Taeb, A., Tetrahedron, 2002, vol. 58, no. 13, p. 2621. https://doi.org/10.1016/S0040-4020(02)00130-8

    Article  CAS  Google Scholar 

  21. Nguyen, H.V., Matsubara, R., and Kobayashi, S., Angew. Chem. Int. Ed., 2009, vol. 48, no. 32, p. 5927. https://doi.org/10.1002/anie.200900309

    Article  CAS  Google Scholar 

  22. Matsubara, R., Berthiol, F., and Kobayashi, S., J. Am. Chem. Soc., 2008, vol. 130, no. 6, p. 1804. https://doi.org/10.1021/ja077054u

    Article  CAS  PubMed  Google Scholar 

  23. Bassindale, A.R. and Posner, T.B., J. Organomet. Chem., 1979, vol. 175, no. 2, p. 273. https://doi.org/10.1016/S0022-328X(00)84548-9

    Article  CAS  Google Scholar 

  24. Jancke, H., Engelhardt, G., Wagner, S., Dirnens, W., Herzog, G., Thieme, E., and Rühlmann, K., J. Organomet. Chem., 1977, vol. 134, no. 1, p. 21. https://doi.org/10.1016/S0022-328X(00)93609-X

    Article  CAS  Google Scholar 

  25. Fukui, M., Itoh, K., Ishii, Y., J. Chem. Soc. Perkin Trans. 2, 1972, no. 9, p. 1043. https://doi.org/10.1039/P29720001043

    Article  Google Scholar 

  26. Albanov, A.I., Larin, M.F., Pestunovich, V.A., Voronkov, M.G., Kramarova, E.P., and Baukov, Yu.I., Zh. Obshch. Khim., 1981, vol. 51, no. 2, p. 488.

    CAS  Google Scholar 

  27. Otter, J.C., Adamson, C.L., Yoder, C.H., and Rheingold, A.L., Organometallics, 1990, vol. 9, no. 5, p. 1557. https://doi.org/10.1021/om00119a030.

    Article  CAS  Google Scholar 

  28. Padrela, L., Zeglinski, J., and Ryan, K., Cryst. Growth Des., 2019, vol. 19, no. 2, p. 613. https://doi.org/10.1021/acs.cgd.8b01015

    Article  CAS  Google Scholar 

  29. Sheldrick, G.M., Acta Crystallogr. (A), 2008, vol. 64, p. 112. https://doi.org/10.1107/S0108767307043930

    Article  CAS  Google Scholar 

  30. Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Scalmani, G., Barone, V., Mennucci, B., Petersson, G.A., Nakatsuji, H., Caricato, M., Li, X., Hratchian, H.P., Izmaylov, A.F., Bloino, J., Zheng, G., Sonnenberg, J.L., Hada, M., Ehara, M., Toyota, K., Fukuda, R., Hasegawa, J., Ishida, M., Nakajima, T., Honda, Y., Kitao, O., Nakai, H., Vreven, T., Montgomery, J.A., Jr., Peralta, J.E., Ogliaro, F., Bearpark, M., Heyd, J.J., Brothers, E., Kudin, K.N., Staroverov, V.N., Kobayashi, R., Normand, J., Raghavachari, K., Rendell, A., Burant, J.C., Iyengar, S.S., Tomasi, J., Cossi, M., Rega, N., Millam, J.M., Klene, M., Knox, J.E., Cross, J.B., Bakken, V., Adamo, C., Jaramillo, J., Gomperts, R., Stratmann, R.E., Yazyev, O., Austin, A.J., Cammi, R., Pomelli, C., Ochterski, J.W., Martin, R.L., Morokuma, K., Zakrzewski, V.G., Voth, G.A., Salvador, P., Dannenberg, J.J., Dapprich, S., Daniels, A.D., Farkas, O., Foresman, J.B., Ortiz, J.V., Cioslowski, J., and Fox, D.J., Gaussian 09, Revision A.01, Gaussian, Inc., Wallingford CT, 2009.

  31. Taylor, J.E., Jones, M.D., Williams, J.M.J., and Bull, S.D., J. Org. Chem., 2012, vol. 77, no, p. 2808. https://doi.org/10.1021/jo202647f

    Article  CAS  PubMed  Google Scholar 

Download references

Funding

This study was financially supported by the Russian Foundation for Basic Research (project no. 18-33-00368-mol_a) and performed using the equipment of the Baikal Analytical Center for Collective Usage, Siberian Branch, RAS.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to I. V. Sterkhova.

Ethics declarations

No conflict of interest was declared by the authors.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Nikonov, A.Y., Sterkhova, I.V., Kolyvanov, N.A. et al. O-Trimethylsilyl-N-phenylsulfonylacetimidate: Synthesis and Structure. Russ J Gen Chem 90, 1641–1645 (2020). https://doi.org/10.1134/S1070363220090091

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070363220090091

Keywords:

Navigation