Synthesis and Characterisation of Diaryl Furoxans

Abstract

The paper discusses the synthesis, characterisation, and performance evaluation of diaryl furoxans namely, bis-phenyl-3,4-furoxan (5) and bis-(4'-nitrophenyl)-3,4-furoxan (6). The molecules have been synthesised on the lines of reported method by cyclodimerisation of the nitrile oxides generated from benzaldoxime and p-nitro benzaldoxime, respectively. The synthesised furoxans (5 ) and (6) were characterised by the elemental analysis, UV, IR, and 1 H NMR spectroscopy. The hazard characteristics (impact and friction sensitivity) confirm that the compounds are safe to handle. The oxygen balance, velocity of detonation and detonation pressure have been computed. The detonation velocity and pressure along with oxygen balance increased with the substitution of nitro group in the benzene ring, as expected. The thermogravimetric studies on promising compound (6) brings out that maximum weight loss occurs at decomposition temperature of 259-260 °C.

Multifunctionalization of Polymers by Strain-Promoted Cycloadditions

“…35 For example, benzohydroxamoyl chloride has been reported to dimerize to give bis-phenyl-3,4-furoxan when treated with triethylamine at room temperature. 36 Also, nitrile oxides formed by BAIB-mediated oxidation of the corresponding oximes, can react with acetic acid to form N -acetoxy amides and for example, oxidation of benzaldoxime with BAIB in absence of dipolarophiles did not give the dimerization adduct but provided N -acetoxy benzamide. 37 When polymer 3a was treated with BAIB in absence of DIBO, a high molecular weight shoulder was observed in the GPC chromatogram of the resulting product (Figure S2).…”

“…Nitrile oxides are reactive species that can dimerize to form furoxans . For example, benzohydroxamoyl chloride has been reported to dimerize to give bis(phenyl)-3,4-furoxan when treated with triethylamine at room temperature . Also, nitrile oxides formed by BAIB-mediated oxidation of the corresponding oximes, can react with acetic acid to form N -acetoxy amides and for example, oxidation of benzaldoxime with BAIB in absence of dipolarophiles did not give the dimerization adduct but provided N -acetoxy benzamide .…”