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Stereoselective epoxidation of 4-fluoro-4-nitrocyclohexenes

Victoria Eduardovna Shambalova 1
Victoria Eduardovna Shambalova
, 
Roman Victorovich Larkovich 1
Roman Victorovich Larkovich
,  , 
Alexander Sergeyevich Aldoshin 1
Alexander Sergeyevich Aldoshin
, 
Konstantin Alexandrovich Lyssenko 1
Konstantin Alexandrovich Lyssenko
, 
Valentin Georgievich Nenajdenko 1
Valentin Georgievich Nenajdenko
1 Department of Chemistry, M.V. Lomonosov Moscow State University, Moscow, Russian Federation
10.1016/j.mencom.2023.06.007
Published 2023-06-13
Communication , Volume 33, Issue 4, 463-465
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Shambalova V. E. et al. Stereoselective epoxidation of 4-fluoro-4-nitrocyclohexenes // Mendeleev Communications. 2023. Vol. 33. No. 4. pp. 463-465.
GOST all authors (up to 50) Copy
Shambalova V. E., Larkovich R. V., Ponomarev S. A., Aldoshin A. S., Lyssenko K. A., Nenajdenko V. G. Stereoselective epoxidation of 4-fluoro-4-nitrocyclohexenes // Mendeleev Communications. 2023. Vol. 33. No. 4. pp. 463-465.
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TY - JOUR
DO - 10.1016/j.mencom.2023.06.007
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2023.06.007
TI - Stereoselective epoxidation of 4-fluoro-4-nitrocyclohexenes
T2 - Mendeleev Communications
AU - Shambalova, Victoria Eduardovna
AU - Larkovich, Roman Victorovich
AU - Ponomarev, Savva Andreevich
AU - Aldoshin, Alexander Sergeyevich
AU - Lyssenko, Konstantin Alexandrovich
AU - Nenajdenko, Valentin Georgievich
PY - 2023
DA - 2023/06/13
PB - Mendeleev Communications
SP - 463-465
IS - 4
VL - 33
ER -
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@article{2023_Shambalova,
author = {Victoria Eduardovna Shambalova and Roman Victorovich Larkovich and Savva Andreevich Ponomarev and Alexander Sergeyevich Aldoshin and Konstantin Alexandrovich Lyssenko and Valentin Georgievich Nenajdenko},
title = {Stereoselective epoxidation of 4-fluoro-4-nitrocyclohexenes},
journal = {Mendeleev Communications},
year = {2023},
volume = {33},
publisher = {Mendeleev Communications},
month = {Jun},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2023.06.007},
number = {4},
pages = {463--465},
doi = {10.1016/j.mencom.2023.06.007}
}
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MLA Copy
Shambalova, Victoria Eduardovna, et al. “Stereoselective epoxidation of 4-fluoro-4-nitrocyclohexenes.” Mendeleev Communications, vol. 33, no. 4, Jun. 2023, pp. 463-465. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2023.06.007.

Keywords

Diels–Alder reaction
diols.
epoxidation
hydrolysis
nitrostyrenes
organofluorine compounds
ring-opening

Abstract

Novel fluorinated α-epoxycyclohexanes were synthesized in up to 96% yields by epoxidation of the Diels-Alder adducts of β-fluoro-β-nitrostyrenes and 2,3-dimethylbuta-1,3-diene. The epoxidation with m-chloroperoxybenzoic acid and subsequent hydrolysis into diols were found to proceed in a highly stereoselective manner.

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