Home / Publications / Replacement of the nitro groups in 1,3,5-trinitrobenzene on treatment with polyfluorinated alcohols

Replacement of the nitro groups in 1,3,5-trinitrobenzene on treatment with polyfluorinated alcohols

Svyatoslav Arkad'evich Shevelev 1
Svyatoslav Arkad'evich Shevelev
, 
Mikhail Dmitrievich Dutov 1
Mikhail Dmitrievich Dutov
, 
Maksim Aleksandrovich Korolev 1
Maksim Aleksandrovich Korolev
, 
Oleg Yuryevich Sapozhnikov 1
Oleg Yuryevich Sapozhnikov
, 
Aleksandr L'vovich Rusanov 2
Aleksandr L'vovich Rusanov
10.1070/MC1998v008n02ABEH000896
Published 1998-04-28
Communication , Volume 8, Issue 2, 69-70
16
Share
Cite this
GOST
 | 
Cite this
GOST Copy
Shevelev S. A. et al. Replacement of the nitro groups in 1,3,5-trinitrobenzene on treatment with polyfluorinated alcohols // Mendeleev Communications. 1998. Vol. 8. No. 2. pp. 69-70.
GOST all authors (up to 50) Copy
Shevelev S. A., Dutov M. D., Korolev M. A., Sapozhnikov O. Y., Rusanov A. L. Replacement of the nitro groups in 1,3,5-trinitrobenzene on treatment with polyfluorinated alcohols // Mendeleev Communications. 1998. Vol. 8. No. 2. pp. 69-70.
RIS
 | 
Cite this
RIS Copy
TY - JOUR
DO - 10.1070/MC1998v008n02ABEH000896
UR - https://mendcomm.colab.ws/publications/10.1070/MC1998v008n02ABEH000896
TI - Replacement of the nitro groups in 1,3,5-trinitrobenzene on treatment with polyfluorinated alcohols
T2 - Mendeleev Communications
AU - Shevelev, Svyatoslav Arkad'evich
AU - Dutov, Mikhail Dmitrievich
AU - Korolev, Maksim Aleksandrovich
AU - Sapozhnikov, Oleg Yuryevich
AU - Rusanov, Aleksandr L'vovich
PY - 1998
DA - 1998/04/28
PB - Mendeleev Communications
SP - 69-70
IS - 2
VL - 8
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors) Copy
@article{1998_Shevelev,
author = {Svyatoslav Arkad'evich Shevelev and Mikhail Dmitrievich Dutov and Maksim Aleksandrovich Korolev and Oleg Yuryevich Sapozhnikov and Aleksandr L'vovich Rusanov},
title = {Replacement of the nitro groups in 1,3,5-trinitrobenzene on treatment with polyfluorinated alcohols},
journal = {Mendeleev Communications},
year = {1998},
volume = {8},
publisher = {Mendeleev Communications},
month = {Apr},
url = {https://mendcomm.colab.ws/publications/10.1070/MC1998v008n02ABEH000896},
number = {2},
pages = {69--70},
doi = {10.1070/MC1998v008n02ABEH000896}
}
MLA
Cite this
MLA Copy
Shevelev, Svyatoslav Arkad'evich, et al. “Replacement of the nitro groups in 1,3,5-trinitrobenzene on treatment with polyfluorinated alcohols.” Mendeleev Communications, vol. 8, no. 2, Apr. 1998, pp. 69-70. https://mendcomm.colab.ws/publications/10.1070/MC1998v008n02ABEH000896.

Abstract

Depending on the conditions, polyfluorinated alcohols RfCH2OH [Rf = CF3, H(CF2)n; n = 2, 4, 6, 8] replace one or two nitro groups in 1,3,5-trinitrobenzene in the presence of K2CO3 in N-methylpyrrolidone to give the previously unknown 1-polyfluoroalkoxy-3,5-dinitrobenzenes or 1,3-di(polyfluoroalkoxy)-5-nitrobenzenes; the reaction is successful due to the high acidity of RfCH2OH (pKa ≈ 12).

References

1.
10.1070/MC1998v008n02ABEH000896_bib1
Buncel
Electron Deficient Aromatic and Heteroaromatic Base Interaction. The Chemistry of Anionic Sigma-Complexes, 1984
3.
10.1070/MC1998v008n02ABEH000896_bib3
Terrier
Nucleophilic Aromatic Displacement. The Influence of the Nitro Group, 1991
4.
Shevelev S.A., Dutov M.D., Vatsadze I.A., Serushkina O.V., Rusanov A.L., Andrievskii A.M.
Mendeleev Communications, 1995
5.
Shevelev S.A., Dutov M.D., Vatsadze I.A., Korolev M.A., Rusanov A.L.
Mendeleev Communications, 1996
6.
10.1070/MC1998v008n02ABEH000896_bib6
Shevelev
Izv. Akad. Nauk, Ser. Khim., 1995
7.
10.1070/MC1998v008n02ABEH000896_bib7
Khalfina
Zh. Org. Khim., 1996
8.
10.1070/MC1998v008n02ABEH000896_bib8
Tabatskaya
Zh. Org. Khim., 1996
10.
Calculation of the pKa values of alcohols from .sigma. constants and from the carbonyl frequencies of their esters
Takahashi S., Cohen L.A., Miller H.K., Peake E.G.
Journal of Organic Chemistry, 1971
11.
Equilibrium acidities in dimethyl sulfoxide solution
Bordwell F.G.
Accounts of Chemical Research, 1988
12.
Meisenheimer complexes derived from hydroxide ion
Fyfe G.A., Foreman M.I., Foster R.
Tetrahedron Letters, 1969
14.
Formation of Meisenheimer–Jackson complexes in a non-polar solvent
Butler A.R.
Journal of the Chemical Society Perkin Transactions 1, 1975
16.
10.1070/MC1998v008n02ABEH000896_bib16
Knyazev
Zh. Org. Khim., 1976
17.
Synthesis and properties of new polyimides containing flourinated alkoxy side chains
Ichino T., Sasaki S., Matsuura T., Nishi S.
Journal of Polymer Science, Part A: Polymer Chemistry, 1990