Efficient synthesis of N-(chloromethyl)nitramines via TiCl4-catalyzed chlorodeacetoxylation
Publication type: Journal Article
Publication date: 2022-08-19
scimago Q2
wos Q3
SJR: 0.493
CiteScore: 5.0
Impact factor: 2.5
ISSN: 11440546, 13699261
Materials Chemistry
General Chemistry
Catalysis
Abstract
The nitramino group is an important motif in energetic compounds, positively influencing the oxygen and nitrogen content, density and enthalpy of formation. Herein, a simple, mild and general procedure has been developed for the preparation of diverse N-(chloromethyl)nitramine building blocks from readily available N-(acetoxymethyl)nitramines via a TiCl4-catalyzed chlorodeacetoxylation with SOCl2. This new protocol allows the conversion of both mono- and di(acetoxymethyl) precursors that contain one to four nitramino groups into functionalized chloromethyl compounds in excellent yields.
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Gribov P. S., Suponitsky K. Y., Sheremetev A. B. Efficient synthesis of N-(chloromethyl)nitramines via TiCl4-catalyzed chlorodeacetoxylation // New Journal of Chemistry. 2022. Vol. 46. No. 36. pp. 17548-17553.
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Gribov P. S., Suponitsky K. Y., Sheremetev A. B. Efficient synthesis of N-(chloromethyl)nitramines via TiCl4-catalyzed chlorodeacetoxylation // New Journal of Chemistry. 2022. Vol. 46. No. 36. pp. 17548-17553.
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RIS
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TY - JOUR
DO - 10.1039/d2nj03521a
UR - https://xlink.rsc.org/?DOI=D2NJ03521A
TI - Efficient synthesis of N-(chloromethyl)nitramines via TiCl4-catalyzed chlorodeacetoxylation
T2 - New Journal of Chemistry
AU - Gribov, Pavel S
AU - Suponitsky, Kyrill Yu.
AU - Sheremetev, Aleksei B.
PY - 2022
DA - 2022/08/19
PB - Royal Society of Chemistry (RSC)
SP - 17548-17553
IS - 36
VL - 46
SN - 1144-0546
SN - 1369-9261
ER -
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BibTex (up to 50 authors)
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@article{2022_Gribov,
author = {Pavel S Gribov and Kyrill Yu. Suponitsky and Aleksei B. Sheremetev},
title = {Efficient synthesis of N-(chloromethyl)nitramines via TiCl4-catalyzed chlorodeacetoxylation},
journal = {New Journal of Chemistry},
year = {2022},
volume = {46},
publisher = {Royal Society of Chemistry (RSC)},
month = {aug},
url = {https://xlink.rsc.org/?DOI=D2NJ03521A},
number = {36},
pages = {17548--17553},
doi = {10.1039/d2nj03521a}
}
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MLA
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Gribov, Pavel S., et al. “Efficient synthesis of N-(chloromethyl)nitramines via TiCl4-catalyzed chlorodeacetoxylation.” New Journal of Chemistry, vol. 46, no. 36, Aug. 2022, pp. 17548-17553. https://xlink.rsc.org/?DOI=D2NJ03521A.