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Tuning Green Explosives through SNAr Chemistry.
Nikitin, Sergei; Diness, Frederik.
Afiliación
  • Nikitin S; Department of Chemistry, Roskilde University, Universitetsvej 1, 4000, Roskilde, Denmark.
  • Diness F; Department of Chemistry, University of Copenhagen, Universitetsparken 5, 2100, Copenhagen, Denmark.
Chem Asian J ; 19(13): e202400212, 2024 Jul 02.
Article en En | MEDLINE | ID: mdl-38602240
ABSTRACT
Reactivity and regioselectivity of SNAr-type fluorine substitution with azide in polyfluorosubstituted nitrobenzenes was studied both theoretically and experimentally. The obtained polyazido-substituted nitrobenzene derivatives were extensively characterized by NMR, IR, HPLC, X-ray, and DFT methods. It was found that the substitution with the azide nucleophile occurs first at the para- and the ortho-positions to the NO2-group and that transazidation reactions also occur here. Thermal decomposition of prepared azidonitrobenzenes was studied both in controlled (kinetic decay) and uncontrolled (explosion) modes. In case of the controlled thermal decomposition of ortho-azidonitrobenzenes, benzofuroxans were found as major products of the reaction unless another azido group was adjacent to the furoxan moiety. The bursting power of azidonitrobenzenes was found to rise gradually with the number of the azide substituents in the aromatic ring.
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: Chem Asian J Año: 2024 Tipo del documento: Article País de afiliación: Dinamarca Pais de publicación: Alemania

Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: Chem Asian J Año: 2024 Tipo del documento: Article País de afiliación: Dinamarca Pais de publicación: Alemania