First Synthesis of Aliphatic Nitro‐NNO‐azoxy Compounds

First Synthesis of Aliphatic Nitro‐NNO‐azoxy Compounds Full article

Journal

European Journal of Organic Chemistry
ISSN: 1434-193X , E-ISSN: 1099-0690

Output data

Year: 2019, Volume: 2019, Number: 1, Pages: 91-94 Pages count : 4 DOI: 10.1002/ejoc.201801533

Authors

Leonov Nikita E. ¹ , Klenov Michael S. ¹ , Anikin Oleg V. ¹ , Churakov Aleksandr M. ¹ , Strelenko Yurii A. ¹ , Monogarov Konstantin A. ² , Tartakovsky Vladimir A. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991 Moscow, Russian Federation
2	Semenov Institute of Chemical Physics, Russian Academy of Sciences, 4 Kosygina Street, Building 1, 119991 Moscow, Russian Federation

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.

Leonov N.E. , Klenov M.S. , Anikin O.V. , Churakov A.M. , Strelenko Y.A. , Monogarov K.A. , Tartakovsky V.A.
First Synthesis of Aliphatic Nitro‐NNO‐azoxy Compounds
European Journal of Organic Chemistry. 2019. V.2019. N1. P.91-94. DOI: 10.1002/ejoc.201801533 WOS Scopus OpenAlex

≡ Web of science:	WOS:000455786200015
≡ Scopus:	2-s2.0-85058099939
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