Leonov, Nikita E.;
Klenov, Michael S.;
Anikin, Oleg V.;
Churakov, Aleksandr M.;
Strelenko, Yurii A.;
Monogarov, Konstantin A.;
Tartakovsky, Vladimir A.
First Synthesis of Aliphatic Nitro‐NNO‐azoxy Compounds
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Media type:
E-Article
Title:
First Synthesis of Aliphatic Nitro‐NNO‐azoxy Compounds
Contributor:
Leonov, Nikita E.;
Klenov, Michael S.;
Anikin, Oleg V.;
Churakov, Aleksandr M.;
Strelenko, Yurii A.;
Monogarov, Konstantin A.;
Tartakovsky, Vladimir A.
Published:
Wiley, 2019
Published in:
European Journal of Organic Chemistry, 2019 (2019) 1, Seite 91-94
Language:
English
DOI:
10.1002/ejoc.201801533
ISSN:
1434-193X;
1099-0690
Origination:
Footnote:
Description:
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.