Abstract
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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