Efficient synthesis of N-(chloromethyl)nitramines via TiCl4-catalyzed chlorodeacetoxylation

Efficient synthesis of N-(chloromethyl)nitramines via TiCl4-catalyzed chlorodeacetoxylation Full article

Journal

New Journal of Chemistry
ISSN: 1369-9261 , E-ISSN: 1144-0546

Output data

Year: 2022, Volume: 46, Number: 36, Pages: 17548-17553 Pages count : 6 DOI: 10.1039/d2nj03521a

Authors

Gribov Pavel S. ¹ , Suponitsky Kyrill ² , Sheremetev Aleksei B. ¹

Affiliations

1	Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow 119991, Russian Federation
2	Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences, Moscow119991, Russian Federation

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.

Gribov P.S. , Suponitsky K. , Sheremetev A.B.
Efficient synthesis of N-(chloromethyl)nitramines via TiCl4-catalyzed chlorodeacetoxylation
New Journal of Chemistry. 2022. V.46. N36. P.17548-17553. DOI: 10.1039/d2nj03521a WOS Scopus OpenAlex

≡ Web of science:	WOS:000847727500001
≡ Scopus:	2-s2.0-85138175551
≡ OpenAlex:	W4292286395