Tuning Green Explosives through SNAr Chemistry
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Tuning Green Explosives through SNAr Chemistry. / Nikitin, Sergei; Diness, Frederik.
I: Chemistry - An Asian Journal, 2024.Publikation: Bidrag til tidsskrift › Tidsskriftartikel › Forskning › fagfællebedømt
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TY - JOUR
T1 - Tuning Green Explosives through SNAr Chemistry
AU - Nikitin, Sergei
AU - Diness, Frederik
PY - 2024
Y1 - 2024
N2 - Reactivity and regioselectivity of SNAr-type fluorine substitution with azide in polyfluoronitrobenzenes was studied both theoretically and experimentally. The obtained polyazidonitrobenzene 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.
AB - Reactivity and regioselectivity of SNAr-type fluorine substitution with azide in polyfluoronitrobenzenes was studied both theoretically and experimentally. The obtained polyazidonitrobenzene 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.
U2 - 10.1002/asia.202400212
DO - 10.1002/asia.202400212
M3 - Journal article
C2 - 38602240
JO - Chemistry - An Asian Journal
JF - Chemistry - An Asian Journal
SN - 1861-4728
M1 - e202400212
ER -
ID: 391674440