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Reactivity of the low-nucleophilic N-dinitromethyl carbanion center in polynitromethylazoles

Victor Vladimirovich Semenov 1
Victor Vladimirovich Semenov
, 
Svyatoslav Arkad'evich Shevelev 1
Svyatoslav Arkad'evich Shevelev
10.1016/j.mencom.2010.11.010
Published 2010-11-02
Communication , Volume 20, Issue 6, 332-334
20
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Semenov V. V., Shevelev S. A. Reactivity of the low-nucleophilic N-dinitromethyl carbanion center in polynitromethylazoles // Mendeleev Communications. 2010. Vol. 20. No. 6. pp. 332-334.
GOST all authors (up to 50) Copy
Semenov V. V., Shevelev S. A. Reactivity of the low-nucleophilic N-dinitromethyl carbanion center in polynitromethylazoles // Mendeleev Communications. 2010. Vol. 20. No. 6. pp. 332-334.
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TY - JOUR
DO - 10.1016/j.mencom.2010.11.010
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2010.11.010
TI - Reactivity of the low-nucleophilic N-dinitromethyl carbanion center in polynitromethylazoles
T2 - Mendeleev Communications
AU - Semenov, Victor Vladimirovich
AU - Shevelev, Svyatoslav Arkad'evich
PY - 2010
DA - 2010/11/02
PB - Mendeleev Communications
SP - 332-334
IS - 6
VL - 20
ER -
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@article{2010_Semenov,
author = {Victor Vladimirovich Semenov and Svyatoslav Arkad'evich Shevelev},
title = {Reactivity of the low-nucleophilic N-dinitromethyl carbanion center in polynitromethylazoles},
journal = {Mendeleev Communications},
year = {2010},
volume = {20},
publisher = {Mendeleev Communications},
month = {Nov},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2010.11.010},
number = {6},
pages = {332--334},
doi = {10.1016/j.mencom.2010.11.010}
}
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Semenov, Victor Vladimirovich, and Svyatoslav Arkad'evich Shevelev. “Reactivity of the low-nucleophilic N-dinitromethyl carbanion center in polynitromethylazoles.” Mendeleev Communications, vol. 20, no. 6, Nov. 2010, pp. 332-334. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2010.11.010.

Abstract

Reactivity of N-dinitromethylazoles possessing extremely high CH acidity (pKa –1.75–0) was investigated in Michael, Henry and alkylation reactions. N-Dinitromethylazole K-salts and hexamethylenetetramine under acidic conditions yield bis-Mannich bases (86–100%) whose secondary amine moiety can be N-nitrated with HNO3–H2SO4 system.

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