First Synthesis of Aliphatic Nitro-NNO -azoxy Compounds
The first aliphatic nitro‐NNO‐azoxy compounds were synthesized by substitutive nitration of appropriate tert‐butyl‐NNO‐azoxy compounds with nitronium tetrafluoroborate. Nitro(nitro‐NNO‐azoxy)methane (1), (tert‐butyl‐NNO‐azoxy)(nitro‐NNO‐azoxy)methane (2), bis(nitro‐NNO‐azoxy)methane (3), and 2‐nitro‐2‐(nitro‐NNO‐azoxy)propane (4) were prepared. Compound 4 with the nitro‐NNO‐azoxy group bound with the tertiary C atom appeared most stable (DSC, onset temperature of decomposition 104 °C). Compound 2 was less stable (DSC, onset temperature 88 °C). Compounds with strong electron withdrawing substituents had the least stability, assumingly, due to rather high acidity of CH protons alongside with instability of C‐anions of nitro‐NNO‐azoxy compounds.
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