Skip to main content
SpringerLink
Log in

Reactivity of heterocyclic α-aminomethylsilanes with alcohols

  • SHORT COMMUNICATION
  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Alkoxylation of N-substituted heterocyclic aminomethylsilyl moieties was studied using primary and tertiary alcohols. The reaction of 4-(silylmethyl)morpholine and 1-(silylmethyl)azepane under catalyst- and solvent-free conditions leads to the formation of dialkoxy- and trialkoxyaminomethylsilyl derivatives. The methanolysis of 4-(silylmethyl)morpholine resulted in trimethoxyaminomethylsilane formation as the main product and two byproducts, i.e., tetramethoxysilane and N-methylmorpholine.

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. (a) Lebedev, A. V.; Minas'yan, R. M.; Abramkin, A. M.; Sheludyakov, V. D.; Kuzmina, N. E.; Lebedeva, A. B.; Surikov, G. E.; Rybakov, V. B. Russ. J. Gen. Chem. 2016, 86, 1859. [Zh. Obshch. Khim. 2016, 86, 1321.] (b) Picard, J.-P. Can. J. Chem. 2000, 78, 1363. (c) Picard, J.-P. In Advances in Organometallic Chemistry; Academic Press, 2004, Vol. 52, p. 175. (d) Woski, M.; Berger, R. J. F.; Mitzel, N. W. Dalton Trans. 2008, 41, 5652. (e) Ohmura, T.; Nishiura, H.; Suginome, M. Organometallics 2017, 36, 4298.

  2. (a) Feshin, V. P.; Romanenko, L. S.; Voronkov, M. G. Russ. Chem. Rev. 1981, 50, 248 [Usp. Khim. 1981, 50, 460.] (b) Waerder, B.; Steinhauer, S.; Reuter, C. G.; Bader, J.; Neumann, B.; Stammler, H. G.; Vishnevskiy, Y. V.; Hoge, B.; Mitzel, N. W. Dalton Trans. 2015, 44, 13347.

  3. Mitzel, N. W.; Kiener, C.; Rankin, D. W. H. Organometallics 1999, 18, 3437.

    Article  CAS  Google Scholar 

  4. Berkefeld, A.; Guerra, C. F.; Bertermann, R.; Troegel, D.; Daiß, J. O.; Stohrer, J.; Bickelhaupt, F. M.; Tacke, R. Organometallics 2014, 33, 2721.

    Article  CAS  Google Scholar 

  5. Lukevits, E.; Sleiksha, I.; Liepin'sh, E.; Shat-ts, V. D.; Zitsmane, I.; Purvinya, A. Chem. Heterocycl. Compd. 1991, 27, 1319. [Khim. Geterotsikl. Soedin. 1991, 27, 1644.]

  6. (a) Pfeiffer, J. Alpha Silanes – New Building Blocks for High Performance Coatings; Wacker Chemie: München, 2006. (b) Schindler, W. Alpha-Silane-Terminated Polymers as Novel Binders for Fast Curing Elastic Adhesives; Wacker Chemie: München, 2005. (c) Xu, H.; Gao, Y.; Liu, Z.; Bei, Y. Materials 2018, 11, 1526.

  7. (a) Mitzel, N. W.; Vojinović, K.; Foerster, T.; Robertson, H. E.; Borisenko, K. B.; Rankin, D. W. H. Chem.–Eur. J. 2005, 11, 5114. (b) Whitmore, F. C.; Sommer, L. H. J. Am. Chem. Soc. 1946, 68, 481.

  8. Yin, Y.; Zhang, Y.; Chi, Z.; Xu, J. Eur. Polym. J. 2008, 44, 2284.

  9. Schulze zur Wiesche, E., US Patent 2014/0271750 A1.

  10. (a) Brook, M. A. Silicon in Organic, Organometallic, and Polymer Chemistry; J. Wiley and Sons: New York, 2000, p. 680. (b) Fuchs, P. L. Reagents for Silicon-Mediated Organic Synthesis; Wiley-Blackwell, 2013, p. 816.

  11. (a) Lukevits, E.; Luse, V.; Zitsmane, I.; Liepin'sh, E.; Trushule, M.; Germane, S.; Augustane, I.; Verovskii, V. N.; Prodanchuk, N. G.; Deineka, S. E.; Nivalov, V. N. Chem. Heterocycl. Compd. 1991, 27, 1328. [Khim. Geterotsikl. Soedin. 1991, 1653.] (b) Lukevits, E.; Dremova, V. P.; Simchenko, L. I.; Voronkov, M. G. Pharm. Chem. J. 1974, 8, 611. [Khim.-Farm. Zh. 1974, 8(10), 29.]

  12. (a) Voronkov, M. G.; D'yakov, V. M. Silatrany (Silatranes) [in Russian]; Nauka: Novosibirsk, 1978, p. 208. (b) Puri, J. K.; Singh, R.; Chahal, V. K. Chem. Soc. Rev. 2011, 40, 1791.

  13. (a) Erchak, N.; Olszewska, E.; Kalvinsh, I.; Liepinsh, E.; Belyakov, S.; Sobolev, A.; Arsenyan, P. Chem. Heterocycl. Compd. 2015, 50, 1506. [Khim. Geterotsikl. Soedin. 2014, 1634.] (b) Sperlich, J.; Becht, J.; Mühleisen, M.; Wagner, S. A.; Mattern, G.; Tacke, R. Z. Naturforsch., B: J. Chem. Sci. 1993, 48, 1693. (c) Tacke, R.; Burschka, C.; Heermann, J.; Richter, I.; Wagner, B.; Willeke, R. Eur. J. Inorg. Chem. 2001, 2211. (d) Bertermann, R.; Biller, A.; Kaupp, M.; Penka, M.; Seiler, O.; Tacke, R. Organometallics 2003, 22, 4104.

  14. Eaborn, C. Organosilicon Compounds; Butterworths Scientific Publications, 1960, p. 200.

  15. Lee, V. Y. Organosilicon Compounds. Theory and Experiment (Synthesis); Academic Press, 2017.

  16. Toutov, A. A.; Betz, K. N.; Haibach, M. C.; Romine, A. M.; Grubbs, R. H. Org. Lett. 2016, 18, 5776.

    Article  CAS  Google Scholar 

  17. Lukevics, E.; Dzintara, M. J. Organomet. Chem. 1985, 295, 265.

    Article  CAS  Google Scholar 

  18. Boyer, J.; Corriu, R. J. P.; Perz, R.; Reye, C. J. Organomet. Chem. 1978, 157, 153.

    Article  CAS  Google Scholar 

  19. (a) Ventura-Espinosa, D.; Sabater, S.; Carretero-Cerdán, A.; Baya, M.; Mata, J. A. ACS Catal. 2018, 8, 2558. (b) Vijjamarri, S.; Chidara, V. K.; Rousova, J.; Du, G. Catal. Sci. Technol. 2016, 6, 3886.

  20. (a) Harinath, A.; Bhattacharjee, J.; Anga, S.; Panda, T. K. Aust. J. Chem. 2017, 70, 724. (b) Lorenz, C.; Schubert, U. Chem. Ber. 1995, 128, 1267.

  21. Skrodzki, M.; Zaranek, M.; Witomska, S.; Pawluc, P. Catalysts 2018, 8, 618.

    Article  Google Scholar 

  22. Pypowski, K.; Koval', T. A.; Erchak, N. P. Russ. J. Gen. Chem. 2005, 75, 1674. [Zh. Obshch. Khim. 2005, 75, 1753.]

  23. (a) Lukevits, E.; Moskovich, R. Ya.; Liepin'sh, E.; Yankovskaya, I. S. Zh. Obshch. Khim. 1976, 46, 604. (b) Lukevits, E.; Pestunovich, A. E.; Voronkov, M. G. Chem. Heterocycl. Compd. 1971, 4, 689. [Khim. Geterotsikl. Soedin. 1968, 949.]

  24. (a) Labrecque, D.; Nwe, K. T.; Chan, T. H. Organometallics 1994, 13, 332. (b) Adima, A.; Bied, C.; Moreau, J. J. E.; Wong Chi Man, M. Eur. J. Org. Chem. 2004, 2582.

  25. Yin, B.; Huang, Y.; Wang, G.; Wang, Y. J. Mol. Model. 2010, 16, 437.

    Article  CAS  Google Scholar 

  26. Parnes, Z. N.; Bolestova, G. I. Synthesis 1984, 991.

  27. Stańczyk, W.; Chojnowski, J. J. Organomet. Chem. 1976, 117, 219.

    Article  Google Scholar 

  28. Moser, W. H. Tetrahedron 2001, 57, 2065.

    Article  CAS  Google Scholar 

  29. Lazareva, N. F.; Brodskaya, E. I. Russ. J. Gen. Chem. 2001, 71, 201. [Zh. Obshch. Khim. 2001, 71, 226.]

  30. Spencer, J. N.; Wolbach, W. S.; Hovick, J. W.; Ansel, L.; Modarress, K. J. J. Solution Chem. 1985, 14, 805.

    Article  CAS  Google Scholar 

  31. (a) Noll, J. E.; Daubert, B. F.; Speier, J. L. J. Am. Chem. Soc. 1951, 73, 3871. (b) Zingler, V. G.; Kelling, H.; Popowski, E. Z. Anorg. Allg. Chem. 1981, 476, 41.

Download references

Author information

Authors and Affiliations

  1. Faculty of Natural Science, Siedlce University of Natural Sciences and Humanities, 54 3 Maja St., 08-110, Siedlce, Poland

    Krzysztof Pypowski & Mariusz Mojzych

Authors
  1. Krzysztof Pypowski
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Mariusz Mojzych
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Krzysztof Pypowski.

Additional information

Published in Khimiya Geterotsiklicheskikh Soedinenii, 2021, 57(3), 320–324

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Pypowski, K., Mojzych, M. Reactivity of heterocyclic α-aminomethylsilanes with alcohols. Chem Heterocycl Comp 57, 320–324 (2021). https://doi.org/10.1007/s10593-021-02910-w

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-021-02910-w

Keywords

Search

Navigation