Home / Publications / Regioselective chelation in the reaction of N-trimethylsilyl-N-acetylglycine N’,N’-dimethylamide with chloro(chloromethyl)dimethylsilane

Regioselective chelation in the reaction of N-trimethylsilyl-N-acetylglycine N’,N’-dimethylamide with chloro(chloromethyl)dimethylsilane

Sergey Yur'evich Bylikin 1, 2
Sergey Yur'evich Bylikin
, 
Alexander Aleksandrovich Korlyukov 1, 3
Alexander Aleksandrovich Korlyukov
, 
Aleksandr Gennad'evich Shipov 1
Aleksandr Gennad'evich Shipov
, 
Dmitry Evgen'evich Arkhipov 1, 3
Dmitry Evgen'evich Arkhipov
, 
Natalia Andreevna Kalashnikova 1
Natalia Andreevna Kalashnikova
, 
Vadim Vital'evich Negrebetsky 1
Vadim Vital'evich Negrebetsky
, 
Yuri Ivanovich Baukov 1
Yuri Ivanovich Baukov
10.1016/j.mencom.2015.03.011
Published 2015-03-06
Communication , Volume 25, Issue 2, 114-116
5
Share
Cite this
GOST
 | 
Cite this
GOST Copy
Bylikin S. Y. et al. Regioselective chelation in the reaction of N-trimethylsilyl-N-acetylglycine N’,N’-dimethylamide with chloro(chloromethyl)dimethylsilane // Mendeleev Communications. 2015. Vol. 25. No. 2. pp. 114-116.
GOST all authors (up to 50) Copy
Bylikin S. Y., Korlyukov A. A., Shipov A. G., Arkhipov D. E., Kalashnikova N. A., Negrebetsky V. V., Baukov Y. I. Regioselective chelation in the reaction of N-trimethylsilyl-N-acetylglycine N’,N’-dimethylamide with chloro(chloromethyl)dimethylsilane // Mendeleev Communications. 2015. Vol. 25. No. 2. pp. 114-116.
RIS
 | 
Cite this
RIS Copy
TY - JOUR
DO - 10.1016/j.mencom.2015.03.011
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2015.03.011
TI - Regioselective chelation in the reaction of N-trimethylsilyl-N-acetylglycine N’,N’-dimethylamide with chloro(chloromethyl)dimethylsilane
T2 - Mendeleev Communications
AU - Bylikin, Sergey Yur'evich
AU - Korlyukov, Alexander Aleksandrovich
AU - Shipov, Aleksandr Gennad'evich
AU - Arkhipov, Dmitry Evgen'evich
AU - Kalashnikova, Natalia Andreevna
AU - Negrebetsky, Vadim Vital'evich
AU - Baukov, Yuri Ivanovich
PY - 2015
DA - 2015/03/06
PB - Mendeleev Communications
SP - 114-116
IS - 2
VL - 25
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors) Copy
@article{2015_Bylikin,
author = {Sergey Yur'evich Bylikin and Alexander Aleksandrovich Korlyukov and Aleksandr Gennad'evich Shipov and Dmitry Evgen'evich Arkhipov and Natalia Andreevna Kalashnikova and Vadim Vital'evich Negrebetsky and Yuri Ivanovich Baukov},
title = {Regioselective chelation in the reaction of N-trimethylsilyl-N-acetylglycine N’,N’-dimethylamide with chloro(chloromethyl)dimethylsilane},
journal = {Mendeleev Communications},
year = {2015},
volume = {25},
publisher = {Mendeleev Communications},
month = {Mar},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2015.03.011},
number = {2},
pages = {114--116},
doi = {10.1016/j.mencom.2015.03.011}
}
MLA
Cite this
MLA Copy
Bylikin, Sergey Yur'evich, et al. “Regioselective chelation in the reaction of N-trimethylsilyl-N-acetylglycine N’,N’-dimethylamide with chloro(chloromethyl)dimethylsilane.” Mendeleev Communications, vol. 25, no. 2, Mar. 2015, pp. 114-116. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2015.03.011.

Abstract

Regioselective reaction of N-trimethylsilyl-N-acetylglycine N’,N’-dimethylamide with chloro(chloromethyl)dimethylsilane yields chlorosilane MeC(O)N(CH2SiMe2Cl)CH2C(O)NMe2 with a five-membered C,O-chelate ring involving the N-acetyl group rather than the six-membered ring involving the N’,N’-dimethylamide fragment. According to X-ray data, the pentacoordinate silicon atom in the product has a TBP environment with the halogen and oxygen atoms in axial positions.

References

1.
(a) D. Kost and I. Kalikhman, in The Chemistry of Organic Silicon Compounds, eds. Z. Rappoport and Y. Apeloig,;1; J. Willey, Chichester, 1998, vol. 2, part 1, p. 1339; (b) M. G. Voronkov, V.A. Pestunovich and Yu. I. Baukov, Organomet. Chem. USSR,;1; 1991, 4, 593 (Metalloorg. Khim., 1991, 4, 1210); (c) C. Chuit, R.J. P. Corriu, C. Reyé and J. C. Young, Chem. Rev., 1993, 93, 1371.
2.
Model of the SN2 nucleophilic substitution at the Si atom: X-ray structural study of N-(halogenodimethylsilylmethyl) lactams
Macharashvili A.A., Shklover V.E., Struchkov Y.T., Oleneva G.I., Kramarova E.P., Shipov A.G., Baukov Y.I.
Journal of the Chemical Society Chemical Communications, 1988
3.
10.1016/j.mencom.2015.03.011_sbref0010b
Baukov Yu.
Zh. Obshch. Khim., 1989
4.
10.1016/j.mencom.2015.03.011_sbref0010c
Artamkina
Zh. Obshch. Khim., 1993
5.
10.1016/j.mencom.2015.03.011_sbref0010d
Artamkina
Zh. Obshch. Khim., 1994
6.
Scheme of hydrolysis of five-coordinate chlorosilanes by X-ray diffraction data
Shipov A.G., Kramarova E.P., Murasheva T.P., Korlyukov A.A., Pogozhikh S.A., Tarasenko S.A., Negrebetskii V.V., Yakovlev I.P., Baukov Y.I.
Russian Journal of General Chemistry, 2011
7.
Stereochemical non-rigidity of complexes of hypercoordinate Group 14 elements
Negrebetsky V.V., Tandura S.N., Baukov Y.I.
Russian Chemical Reviews, 2009
9.
Structures and stereochemical non-rigidity of Si-substituted N-(dimethylsilylmethyl)- and N-(methylphenylsilylmethyl)amides and -lactams
Negrebetsky V.V., Taylor P.G., Kramarova E.P., Bylikin S.Y., Belavin I.Y., Shipov A.G., Bassindale A.R., Baukov Y.I.
Journal of Organometallic Chemistry, 2006
11.
Modelling of the pathway of SN2 intramolecular substitution at the silicon(IV) atom
Sidorkin V.F., Vladimirov V.V., Voronkov M.G., Pestunovich V.A.
Journal of Molecular Structure THEOCHEM, 1991
12.
Modelling SN2 nucleophilic substitution at silicon by structural correlation with X-ray crystallography and NMR spectroscopy
Bassindale A.R., Parker D.J., Taylor P.G., Auner N., Herrschaft B.
Journal of Organometallic Chemistry, 2003
14.
Modelling nucleophilic substitution at silicon in solution, using hypervalent silicon compounds based on 2-pyridones
Bassindale A.R., Borbaruah M., Glynn S.J., Parker D.J., Taylor P.G.
Journal of the Chemical Society Perkin Transactions 2, 1999
16.
(a) A. G. Shipov, E.P. Kramarova, O.B. Artamkina, G.I. Oleneva and Yu. I. Baukov, J. Gen. Chem. USSR, 1991, 61, 1770 (Zh. Obshch. Khim., 1991, 61, 1914); (b) M. Sohail, A.R. Bassindale, P.G. Taylor, A.A. Korlyukov, D.E. Arkhipov, L. Male, S.J. Coles and M. B. Hursthouse, Organometallics, 2013, 32, 1721; (c) A. G. Shipov, E.P. Kramarova, H.C. Fang, D.E. Arkhipov, A.A. Nikolin, S. Yu. Bylikin, V.V. Negrebetsky, A.A. Korlyukov, N.A. Voronina, A.R. Bassindale, P.G. Taylor and Yu. I. Baukov, J. Organomet. Chem., 2013, 741-742, 114; (d) A. A. Nikolin, D.E. Arkhipov, A.G. Shipov, E.P. Kramarova, N.A. Koval’chuk, A.A. Korlyukov, V.V. Negrebetsky, Yu. I. Baukov, A.R. Bassindale, P.G. Taylor, A.A. Bowden and S. Yu. Bylikin, Chem. Heterocycl. Compd., 2011, 47, 1565.(Khim. Geterotsikl. Soedin., 2011, 1869).
17.
Pentacoordinate hydrochlorosilanes with lactamomethyl ligand
Pestunovich V.A., Kirpichenko S.V., Lazareva N.F., Albanov A.I., Voronkov M.G.
Journal of Organometallic Chemistry, 2007
18.
Tables of bond lengths determined by X-ray and neutron diffraction. Part 1. Bond lengths in organic compounds
Allen F.H., Kennard O., Watson D.G., Brammer L., Orpen A.G., Taylor R.
Journal of the Chemical Society Perkin Transactions 2, 1987
21.
M. J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G.A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H.P. Hratchian, A.F. Izmaylov, J. Bloino, G. Zheng, J.L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J.A. Montgomery, Jr., J.E. Peralta, F. Ogliaro, M. Bearpark, J.J. Heyd, E. Brothers, K.N. Kudin, V.N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J.C. Burant, S.S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J.M. Millam, M. Klene, J.E. Knox, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, R.L. Martin, K. Morokuma, V.G. Zakrzewski, G.A. Voth, P. Salvador, J.J. Dannenberg, S. Dapprich, A.D. Daniels, Ö. Farkas, J.B. Foresman, J.V. Ortiz, J. Cioslowski and D. J. Fox, Gaussian 09, Revision D.01, Gaussian, Inc., Wallingford CT, 2009.