Functionalized double-chain surfactant 1 (potassium O,O ‘-didodecylphosphorodithioate) was synthesized. Its small unilamellar vesicles were characterized by dynamic laser light scattering and differential scanning calorimetry and its giant vesicles by phase-contrast optical microscopy. Also, 1's giant vesicles containing fluorescent dye 4a (5-carboxyfluorescein) or 4b [5-(dodecanamido)fluorescein] were characterized by epifluorescence microscopy. In a pH 9.0 borate buffer at 25 °C, vesicular 1 reacted with 2 (2-chloroethyl phenyl sulfide), a simulant for the chemical warfare agent mustard [bis(2-chloroethyl) sulfide], to give 5 [S-[(2-phenylthio)ethyl] O,O‘-didodecylphosphorodithioate], involving capture of reactive intermediate cation 9 (1-phenylthiocyclopropane) by the anion of 1. This reaction was accompanied by the precipitation of 5, which resulted in wounding/destruction of the vesicles and the release of dye 4a (from giant vesicles). The combination of the conversion of 2 into 5 and dye release suggests the potential of vesicular systems for simultaneous decontamination and signaling of chemical agents. 2 hydrolyzed to give only 6 [2-(phenylthio)ethanol] in the pH 9.0 buffer at 25 °C.

The synthesis of dinitroazofurazan (3) was achieved from readily available diaminofurazan (6) in two steps and 20% overall yield. The structure of the energetic material 3 was unequivocally confirmed by X‐ray crystallography and found to have a crystal density of 1.742 g/cm3.

Diaminofurazan (1) was synthesized from glyoxal (2) by an improved two‐step procedure. The N‐mono‐arylmethyl derivatives 4a‐e and N‐N'‐diarylmethyl derivatives 5a‐e of 1 were prepared in good yields by reductive alkylation with the corresponding aryl aldehydes.

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