Reactions of 1,3,5-trinitrobenzene with primary aliphatic alcohols


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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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