Nature Chooses Rings: Synthesis of Silicon-Containing Macrocyclic Peroxides
Roman G. Novikov
1
,
Maxim M Platonov
1
,
Valentin G Lakhtin
2
,
Dmitry E. Arkhipov
3, 4
,
Alexander Korlyukov
3, 4
,
V. V. Chernyshev
5, 6
,
Andy Fitch
7
,
Alexander T Zdvizhkov
1
,
Igor B. Krylov
1
,
Yury V. Tomilov
1
,
Gennady I. Nikishin
1
Publication type: Journal Article
Publication date: 2014-04-21
scimago Q2
wos Q1
SJR: 0.676
CiteScore: 5.1
Impact factor: 2.9
ISSN: 02767333, 15206041
Organic Chemistry
Inorganic Chemistry
Physical and Theoretical Chemistry
Abstract
The reactions of 1,2-bis(dimethylchlorosilyl)ethane (1), 1,2-bis(dimethylchlorosilyl)ethene (6), and 1,2-bis(dimethylchlorosilyl)ethyne (7) with gem-bis(hydroperoxides) 2a–h and 1,1′-bis(hydroperoxy)bis(cycloalkyl)peroxides 4a–c were found to proceed in an unusual way. Thus, the reactions do not give the expected polymeric peroxides; instead, they produce cyclic silicon-containing peroxides containing 2, 4, or 6 silicon atoms in the ring: 9- (3a–h), 12- (5a–c), 18- (8, 12), 24- (9, 10), 27- (13), and 36-membered (11) compounds. The size of the rings produced in the reactions increases in the series 1,2-bis(dimethylchlorosilyl)ethane < 1,2-bis(dimethylchlorosilyl)ethene < 1,2-bis(dimethylchlorosilyl)ethyne. The resulting 9- and 12-membered cyclic peroxides are stable under ambient conditions. These compounds were isolated by chromatography and characterized by 1H, 13C, and 29Si NMR spectroscopy, X-ray diffraction, elemental analysis, and high-resolution mass spectrometry. The yields vary from 77 to 95%. St...
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Metrics
33
Total citations:
33
Citations from 2024:
4
(12.12%)
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GOST
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Arzumanyan A. V. et al. Nature Chooses Rings: Synthesis of Silicon-Containing Macrocyclic Peroxides // Organometallics. 2014. Vol. 33. No. 9. pp. 2230-2246.
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Arzumanyan A. V., Novikov R. G., Terent'ev A. O., Platonov M. M., Lakhtin V. G., Arkhipov D. E., Korlyukov A., Chernyshev V. V., Fitch A., Zdvizhkov A. T., Krylov I. B., Tomilov Y. V., Nikishin G. I. Nature Chooses Rings: Synthesis of Silicon-Containing Macrocyclic Peroxides // Organometallics. 2014. Vol. 33. No. 9. pp. 2230-2246.
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RIS
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TY - JOUR
DO - 10.1021/om500095x
UR - https://doi.org/10.1021/om500095x
TI - Nature Chooses Rings: Synthesis of Silicon-Containing Macrocyclic Peroxides
T2 - Organometallics
AU - Arzumanyan, Ashot V
AU - Novikov, Roman G.
AU - Terent'ev, Alexander O.
AU - Platonov, Maxim M
AU - Lakhtin, Valentin G
AU - Arkhipov, Dmitry E.
AU - Korlyukov, Alexander
AU - Chernyshev, V. V.
AU - Fitch, Andy
AU - Zdvizhkov, Alexander T
AU - Krylov, Igor B.
AU - Tomilov, Yury V.
AU - Nikishin, Gennady I.
PY - 2014
DA - 2014/04/21
PB - American Chemical Society (ACS)
SP - 2230-2246
IS - 9
VL - 33
SN - 0276-7333
SN - 1520-6041
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2014_Arzumanyan,
author = {Ashot V Arzumanyan and Roman G. Novikov and Alexander O. Terent'ev and Maxim M Platonov and Valentin G Lakhtin and Dmitry E. Arkhipov and Alexander Korlyukov and V. V. Chernyshev and Andy Fitch and Alexander T Zdvizhkov and Igor B. Krylov and Yury V. Tomilov and Gennady I. Nikishin},
title = {Nature Chooses Rings: Synthesis of Silicon-Containing Macrocyclic Peroxides},
journal = {Organometallics},
year = {2014},
volume = {33},
publisher = {American Chemical Society (ACS)},
month = {apr},
url = {https://doi.org/10.1021/om500095x},
number = {9},
pages = {2230--2246},
doi = {10.1021/om500095x}
}
Cite this
MLA
Copy
Arzumanyan, Ashot V., et al. “Nature Chooses Rings: Synthesis of Silicon-Containing Macrocyclic Peroxides.” Organometallics, vol. 33, no. 9, Apr. 2014, pp. 2230-2246. https://doi.org/10.1021/om500095x.
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