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New spiro-fused 2-nitrocyclopropanecarboxylates: Synthesis and structure

Vasilii Vasil'evich Pelipko 1
Vasilii Vasil'evich Pelipko
, 
Ruslan Izmailovich Baichurin 1
Ruslan Izmailovich Baichurin
, 
Konstantin Alexandrovich Lyssenko 2, 3
Konstantin Alexandrovich Lyssenko
, 
Evgenii Vladimirovich Kondrashov 4
Evgenii Vladimirovich Kondrashov
, 
Sergey Valentinovich Makarenko 1
Sergey Valentinovich Makarenko
1 Herzen State Pedagogical University of Russia, St. Petersburg, Russian Federation
2 G.V. Plekhanov Russian University of Economics, Moscow, Russian Federation
3 Department of Chemistry, M.V. Lomonosov Moscow State University, Moscow, Russian Federation
10.1016/j.mencom.2023.06.003
Published 2023-06-13
Communication , Volume 33, Issue 4, 451-454
4
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Pelipko V. V. et al. New spiro-fused 2-nitrocyclopropanecarboxylates: Synthesis and structure // Mendeleev Communications. 2023. Vol. 33. No. 4. pp. 451-454.
GOST all authors (up to 50) Copy
Pelipko V. V., Baichurin R. I., Lyssenko K. A., Kondrashov E. V., Makarenko S. V. New spiro-fused 2-nitrocyclopropanecarboxylates: Synthesis and structure // Mendeleev Communications. 2023. Vol. 33. No. 4. pp. 451-454.
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TY - JOUR
DO - 10.1016/j.mencom.2023.06.003
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2023.06.003
TI - New spiro-fused 2-nitrocyclopropanecarboxylates: Synthesis and structure
T2 - Mendeleev Communications
AU - Pelipko, Vasilii Vasil'evich
AU - Baichurin, Ruslan Izmailovich
AU - Lyssenko, Konstantin Alexandrovich
AU - Kondrashov, Evgenii Vladimirovich
AU - Makarenko, Sergey Valentinovich
PY - 2023
DA - 2023/06/13
PB - Mendeleev Communications
SP - 451-454
IS - 4
VL - 33
ER -
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@article{2023_Pelipko,
author = {Vasilii Vasil'evich Pelipko and Ruslan Izmailovich Baichurin and Konstantin Alexandrovich Lyssenko and Evgenii Vladimirovich Kondrashov and Sergey Valentinovich Makarenko},
title = {New spiro-fused 2-nitrocyclopropanecarboxylates: Synthesis and structure},
journal = {Mendeleev Communications},
year = {2023},
volume = {33},
publisher = {Mendeleev Communications},
month = {Jun},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2023.06.003},
number = {4},
pages = {451--454},
doi = {10.1016/j.mencom.2023.06.003}
}
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Pelipko, Vasilii Vasil'evich, et al. “New spiro-fused 2-nitrocyclopropanecarboxylates: Synthesis and structure.” Mendeleev Communications, vol. 33, no. 4, Jun. 2023, pp. 451-454. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2023.06.003.

Keywords

1-halo-1-nitroethenes
3-bromo-3-nitroacrylates
3-methyl-1-phenylpyrazol-5-one
Meldrum’s acid
nitrocyclopropane
spirocyclopropane.

Abstract

Reactions of alkyl 3-bromo-3-nitroacrylates with cyclic CH-acids, Meldrum’s acid or 3-methyl-1-phenylpyrazol-5-one, afford new spiro-fused 2-nitrocyclopropanecarboxylates. In the case of Meldrum’s acid, the products are formed as individual diastereomers. The obtained experimental results are confirmed by quantum chemical calculations (B3LYP/6-311+G(d,p) taking into account solvent effects).

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