Reactions of 1,3,5-trinitrobenzene with primary aliphatic alcohols
- Authors: Dutov M.D.1, Aleksanyan D.R.2, Serushkina O.V.1, Nesterova E.N.1, Shevelev S.A.1
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Affiliations:
- N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
- Gubkin Russian State University of Oil and Gas
- Issue: Vol 67, No 5 (2018)
- Pages: 822-825
- Section: Full Articles
- URL: https://journal-vniispk.ru/1066-5285/article/view/242502
- DOI: https://doi.org/10.1007/s11172-018-2143-2
- ID: 242502
Cite item
Abstract
Analysis of reactions of 1,3,5-trinitrobenzene (TNB) with alcoholates of primary aliphatic alcohols (substitution of the nitro group or generation of σH-complexes at the unsubstituted position of TNB) leads to the conclusion that high basicity of alcoholates (MeONa, EtONa) of unsubstituted primary alcohols promotes formation of σH-complexes, thus preventing nucleophilic substitution of a nitro group. Introduction of electron-withdrawing substitutes (R = HC≡C, H2C = CH, pyridyl) into the alcohol molecule (RCH2OH) reduces the basicity of their alcoholates which makes substitution of nitro groups possible aff ording the corresponding 1-alkoxy-3,5-dinitrobenzenes in the presence of K2CO3 in N-methylpyrrolidone at 80 °C.
About the authors
M. D. Dutov
N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Email: izvan@ioc.ac.ru
Russian Federation, 47 Leninsky prosp., Moscow, 119991
D. R. Aleksanyan
Gubkin Russian State University of Oil and Gas
Author for correspondence.
Email: izvan@ioc.ac.ru
Russian Federation, 65 Leninsky prosp., Moscow, 119991
O. V. Serushkina
N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Email: izvan@ioc.ac.ru
Russian Federation, 47 Leninsky prosp., Moscow, 119991
E. N. Nesterova
N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Email: izvan@ioc.ac.ru
Russian Federation, 47 Leninsky prosp., Moscow, 119991
S. A. Shevelev
N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Email: izvan@ioc.ac.ru
Russian Federation, 47 Leninsky prosp., Moscow, 119991
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