Abstract
The reaction of dichloromethylphenylsilane with tert-butanol in the presence of a hydrogen chloride acceptor gave tert-butoxychloromethylphenylsilane. The product is stable at room temperature for a week, undergoing disproportionation upon more prolonged storage. Its reaction with 2-substituted ethanols XCH2CH2OH (X = Cl, MeNH, PhCH2N, PhN) in the presence of bases gives the corresponding polyfunctional silanes MePhSi(OBut)(OCH2CH2X). Alkylation of such N-substituted derivatives with (chloromethyl)triethoxysilane results in polyfunctional α-silyl amines MePhSi(OBut)OCH2CH2N(R)CH2Si(OEt)3 (R = Me, Bn). The structures of all synthesized compounds were confirmed by IR and multinuclear NMR spectroscopy.
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R. H. Baney, M. Itoh, A. Sakakibara, T. Suzuki, Chem. Rev., 1995, 95, 1409; DOI: https://doi.org/10.1021/cr00037a012.
Silicon Based Polymers, Eds F. Ganachaud, S. Boileau, B. Boury, Springer Science-Business Media B.V., 2008, 298 p.
S. J. Clarson, J. J. Fitzgerald, M. J. Owen, S. D. Smith, Silicones and Silicone-Modified Materials, ACS Symposium series, Washington, DC, 2000, Vol. 729, 607 p.
R. Drake, I. MacKinnon, R. Taylor, Recent advances in the chemistry of siloxane polymers and copolymers, in The Chemistry of Organic Silicon Compounds, Ed. Y. Apeloig, Z. Rappoport, Wiley, Hoboken, 2003, 2217 pp.
D. B. Cordes, P. D. Lickiss, F. Rataboul, Chem. Rev., 2010, 110, 2081; DOI: https://doi.org/10.1021/cr900201r.
L.-W. Xu, L. Li, Z.-H. Shia, Adv. Synth. Catal., 2010, 352, 243; DOI: https://doi.org/10.1002/adsc.200900797.
A. D. Dilman, S. L. Ioffe, Chem. Rev., 2003, 103, 733; DOI: https://doi.org/10.1021/cr020003p.
L. G. Lutz, Chem. Eur. J., 2018, 24, 17881; DOI: https://doi.org/10.1002/chem.201802698.
K. Ando, T. Wada, M. Okumura, H. Sumida, Org. Lett., 2015, 17, 6026; DOI: https://doi.org/10.1021/acs.orglett.5b03008.
D. J. Trader, E. E. Carlson, Org. Lett., 2011, 13, 5652; DOI: https://doi.org/10.1021/o1202376m.
S. Kojima, T. Fukuzaki, A. Yamakawa, Y. Murai, Org. Lett., 2004, 6, 3917; DOI: https://doi.org/10.1021/o10486728.
G. L. Fondong, E. Y. Njua, A. Steiner, C. F. Campana, L. Stahl, Polyhedron, 2011, 30 2856; DOI: https://doi.org/10.1016/j.poly.2011.08.011.
V. D. Sheludyakov, V. I. Zhun, M. K. Ten, Russ. J. Gen. Chem., 1987, 57, 567.
H. Hildebrandt, B. Engels, Z. Anorg. Allg. Chem., 2000, 626, 2, 400; DOI: https://doi.org/10.1002/(SICI)1521-3749(200002)626:2<400:AID-ZAAC400>3.0.CO;2-5.
J. I. Schweizer, L. Meyer, A. Nadj, M. Diefenbach, M. C. Holthausen, Chem. Eur. J., 2016, 22, 14328; DOI: https://doi.org/10.1002/chem.201602724.
E. A. Chernyshev, N. G. Komalenkova, A. A. Tagachenkov, V. G. Bykovchenko, Russ. J. Gen. Chem., 1995, 65, 281.
A. M. Varvarin, L. A. Belyakova, Russ. J. Gen. Chem., 1994, 64, 1771.
A. Kawachi, K. Tamao, Organometallics, 1996, 15, 4653; DOI: https://doi.org/10.1021/om960421i.
T. C. Efthymiou, J.-P. Desaulniers, J. Heterocyclic Chem., 2011, 48, 533; DOI: https://doi.org/10.1002/jhet.532.
P. Ortega, J. F. Bermejo, L. Chonco, E. de Jesus, F. J. de la Mata, G. Fernández, J. C. Flores, R. Gómez, M. J. Serramía, M. A. Muñoz-Fernandez, Eur. J. Inorg. Chem., 2006, 1388; DOI: https://doi.org/10.1002/ejic.200500782.
C. H. Kim, M. E. Lee, D. H. Pae, Organometallics, 1987, 6, 2, 423; DOI: https://doi.org/10.1021/om00145a031.
A. Iwata, H. Tang, A. Kunai, J. Ohshita, Y. Yamamoto, C. Matui, J. Org. Chem., 2002, 67, 5170; DOI: https://doi.org/10.1021/jo020019f.
F. Bertasi, E. Negro, K. Vezzu, V. D. Noto, Int. J. Hydrogen Energy, 2014, 39, 2896; DOI: https://doi.org/10.1016/j.ijhydene.2013.08.005.
S. H. Zeisel, Ann. Nutr. Metab., 2012, 61, 3, 254; DOI: https://doi.org/10.1159/000343120.
S. N. Adamovich, R. G. Mirskov, A. N. Mirskova, M. G. Voronkov, Russ. Chem. Bull., 2012, 61, 1262; DOI: https://doi.org/10.1007/s11172-012-0173-8.
A. Zablotskaya, I. Segal, Yu. Popelis, E. Lukevics, S. Baluja, I. Shestakova, I. Domracheva, Appl. Organomet. Chem., 2006, 20, 721; DOI: https://doi.org/10.1002/aoc.1133.
A. Zablotskaya, I. Segal, Yu. Popelis, S. Grinberga, I. Shestakova, V. Nikolajeva, D. Eze, Appl. Organomet. Chem., 2013, 27, 114; DOI: https://doi.org/10.1002/aoc.2952.
I. Segal, A. Zablotskaya, E. Lukevics, Chem. Heterocycl. Compd., 2005, 41, 613; DOI: https://doi.org/10.1007/s10593-005-0192-6.
J. Sanchez-Nieves, A. J. Perise-Barrios, P. Ortega, A. L. Corbı, A. Domınguez-Soto, M. A. Munoz-Fernandez, R. Gomez, F. J. de la Mata, RSC Adv., 2013, 3, 23445; DOI: https://doi.org/10.1039/C3RA43338B.
A. Zablotskaya, I. Segal, M. Maiorov, D. Zablotsky, A. Mishnev, E. Lukevics, I. Shestakova, I. Domracheva, J. Magnetism Magnetic Materials, 2007, 311, 135; DOI: https://doi.org/10.1016/j.jmmm.2006.11.176.
Pass Online; http://www.pharmaexpert.ru/PASSOnline.
D. B. G. Williams, M. Lawton, J. Org. Chem., 2010, 75, 8351; DOI: https://doi.org/10.1021/jo101589h.
W. L. F. Armarego, C. L. L. Chai, Purification of Laboratory Chemicals, 6th ed., Elsevier, 2009.
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The work was carried out using analytical equipment of the Baikal Center for Collective use of the Siberian Branch of the Russian Academy of Sciences.
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Soldatenko, A.S., Lazareva, N.F. tert-Butoxychloromethylphenylsilane: synthesis and reactivity. Russ Chem Bull 69, 2340–2344 (2020). https://doi.org/10.1007/s11172-020-3033-y
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DOI: https://doi.org/10.1007/s11172-020-3033-y