The reaction of N-trimethylsilyl-amides and -lactams with dimethyl(chloromethyl)chlorosilane. Kinetically controlled formation of (NSi) chelate intermediates, O-[(dimethylchlorosilyl)methyl]imidates and their rearrangement to final(OSi) chelate N-[(dimethylchlorosilyl)methyl]amides and lactams
Тип публикации: Journal Article
Дата публикации: 1989-02-01
scimago Q3
wos Q2
БС2
SJR: 0.385
CiteScore: 4.1
Impact factor: 2.4
ISSN: 0022328X, 18728561
Materials Chemistry
Organic Chemistry
Biochemistry
Inorganic Chemistry
Physical and Theoretical Chemistry
Краткое описание
The multistage character of the reaction of dimethyl(chloromethyl)chlorosilane (I) with N-trimethylsilyl-amides and -lactams (II) was shown by NMR monitoring. Interaction of the reactants starts with transsilylation, leading to Me3SiCl and the corresponding N-[dimethyl(chloromethyl)silyl]amide or -lactam (III). The second stage, intramolecular (dimethylchlorosilyl)methylation of unstable III, proceeds in two directions. A kinetically controlled transformation of III affords previously unknown O-(dimethylchlorosilyl)methylated intermediates, O-[(dimethylchlorosilyl) methyl]imidates (IV) containing a hypervalent ClSiN bond. The already known products, (OSi) chelate N-[(dimethylchlorosilyl)methyl]amides (V), arise from the reaction carried out under thermodynamic control. The same compounds are also formed via the Chapman rearrangement of the intermediates (IV).
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Kalikhman I. D. et al. The reaction of N-trimethylsilyl-amides and -lactams with dimethyl(chloromethyl)chlorosilane. Kinetically controlled formation of (NSi) chelate intermediates, O-[(dimethylchlorosilyl)methyl]imidates and their rearrangement to final(OSi) chelate N-[(dimethylchlorosilyl)methyl]amides and lactams // Journal of Organometallic Chemistry. 1989. Vol. 361. No. 2. pp. 147-155.
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Kalikhman I. D., Albanov A. I., Bannikova O. B., Belousova L. I., Voronkov M. G., Pestunovich V., Shipov A. G., Kramarova E. P., Baukov Yu. I. The reaction of N-trimethylsilyl-amides and -lactams with dimethyl(chloromethyl)chlorosilane. Kinetically controlled formation of (NSi) chelate intermediates, O-[(dimethylchlorosilyl)methyl]imidates and their rearrangement to final(OSi) chelate N-[(dimethylchlorosilyl)methyl]amides and lactams // Journal of Organometallic Chemistry. 1989. Vol. 361. No. 2. pp. 147-155.
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TY - JOUR
DO - 10.1016/0022-328x(89)85379-3
UR - https://doi.org/10.1016/0022-328x(89)85379-3
TI - The reaction of N-trimethylsilyl-amides and -lactams with dimethyl(chloromethyl)chlorosilane. Kinetically controlled formation of (NSi) chelate intermediates, O-[(dimethylchlorosilyl)methyl]imidates and their rearrangement to final(OSi) chelate N-[(dimethylchlorosilyl)methyl]amides and lactams
T2 - Journal of Organometallic Chemistry
AU - Kalikhman, I D
AU - Albanov, A I
AU - Bannikova, O B
AU - Belousova, L I
AU - Voronkov, M. G.
AU - Pestunovich, V.A
AU - Shipov, A G
AU - Kramarova, E P
AU - Baukov, Yu I
PY - 1989
DA - 1989/02/01
PB - Elsevier
SP - 147-155
IS - 2
VL - 361
SN - 0022-328X
SN - 1872-8561
ER -
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@article{1989_Kalikhman,
author = {I D Kalikhman and A I Albanov and O B Bannikova and L I Belousova and M. G. Voronkov and V.A Pestunovich and A G Shipov and E P Kramarova and Yu I Baukov},
title = {The reaction of N-trimethylsilyl-amides and -lactams with dimethyl(chloromethyl)chlorosilane. Kinetically controlled formation of (NSi) chelate intermediates, O-[(dimethylchlorosilyl)methyl]imidates and their rearrangement to final(OSi) chelate N-[(dimethylchlorosilyl)methyl]amides and lactams},
journal = {Journal of Organometallic Chemistry},
year = {1989},
volume = {361},
publisher = {Elsevier},
month = {feb},
url = {https://doi.org/10.1016/0022-328x(89)85379-3},
number = {2},
pages = {147--155},
doi = {10.1016/0022-328x(89)85379-3}
}
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Kalikhman, I. D., et al. “The reaction of N-trimethylsilyl-amides and -lactams with dimethyl(chloromethyl)chlorosilane. Kinetically controlled formation of (NSi) chelate intermediates, O-[(dimethylchlorosilyl)methyl]imidates and their rearrangement to final(OSi) chelate N-[(dimethylchlorosilyl)methyl]amides and lactams.” Journal of Organometallic Chemistry, vol. 361, no. 2, Feb. 1989, pp. 147-155. https://doi.org/10.1016/0022-328x(89)85379-3.