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The first example of fluoro-Meinwald rearrangement

, 
Roman Victorovich Larkovich 1
Roman Victorovich Larkovich
, 
Alexander Sergeyevich Aldoshin 1
Alexander Sergeyevich Aldoshin
, 
Victor Nikolaevich Khrustalev 2, 3
Victor Nikolaevich Khrustalev
, 
Valentin Georgievich Nenajdenko 1
Valentin Georgievich Nenajdenko
1 Department of Chemistry, M.V. Lomonosov Moscow State University, Moscow, Russian Federation
3 Peoples Friendship University of Russia (RUDN University), Moscow, Russian Federation
10.1016/j.mencom.2023.02.012
Published 2023-02-13
Communication , Volume 33, Issue 2, 188-190
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Ponomarev S. A. et al. The first example of fluoro-Meinwald rearrangement // Mendeleev Communications. 2023. Vol. 33. No. 2. pp. 188-190.
GOST all authors (up to 50) Copy
Ponomarev S. A., Larkovich R. V., Aldoshin A. S., Khrustalev V. N., Nenajdenko V. G. The first example of fluoro-Meinwald rearrangement // Mendeleev Communications. 2023. Vol. 33. No. 2. pp. 188-190.
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TY - JOUR
DO - 10.1016/j.mencom.2023.02.012
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2023.02.012
TI - The first example of fluoro-Meinwald rearrangement
T2 - Mendeleev Communications
AU - Ponomarev, Savva Andreevich
AU - Larkovich, Roman Victorovich
AU - Aldoshin, Alexander Sergeyevich
AU - Khrustalev, Victor Nikolaevich
AU - Nenajdenko, Valentin Georgievich
PY - 2023
DA - 2023/02/13
PB - Mendeleev Communications
SP - 188-190
IS - 2
VL - 33
ER -
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@article{2023_Ponomarev,
author = {Savva Andreevich Ponomarev and Roman Victorovich Larkovich and Alexander Sergeyevich Aldoshin and Victor Nikolaevich Khrustalev and Valentin Georgievich Nenajdenko},
title = {The first example of fluoro-Meinwald rearrangement},
journal = {Mendeleev Communications},
year = {2023},
volume = {33},
publisher = {Mendeleev Communications},
month = {Feb},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2023.02.012},
number = {2},
pages = {188--190},
doi = {10.1016/j.mencom.2023.02.012}
}
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MLA Copy
Ponomarev, Savva Andreevich, et al. “The first example of fluoro-Meinwald rearrangement.” Mendeleev Communications, vol. 33, no. 2, Feb. 2023, pp. 188-190. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2023.02.012.

Keywords

acyl fluorides
bicyclo[3.1.0]hex-2-ene-6-carboxylic acids
Diels–Alder reaction
epoxidation
Meinwald rearrangement
nitrostyrene
norbornadiene
norbornene
organofluorine compounds.

Abstract

Novel fluorinated norbornadienes were synthesized in up to 95% yield by the base-induced elimination of HNO2 from 5-fluoro-5-nitro-6-arylbicyclo[2.2.1]hept-2-enes prepared, in turn, by the Diels-Alder reaction of β-fluoro-β-nitrostyrenes with cyclopentadiene. The subsequent epoxidation initiated the Meinwald type rearrangement affording 6-aryl-bicyclo[3.1.0]hex-2-ene-6-carboxylic acid fluorides as individual (1SR,5RS,6RS)-diastereomers. The transformation is the first example of fluoro-Meinwald rearrangement to form the corresponding acyl fluorides.

References

.
Comparison of silver and molybdenum microfocus X-ray sources for single-crystal structure determination
Krause L., Herbst-Irmer R., Sheldrick G.M., Stalke D.
Journal of Applied Crystallography, 2015
.
Radical Nitration-Debromination of α-Bromo-α-fluoroalkenes as a Stereoselective Route to Aromatic α-Fluoronitroalkenes—Functionalized Fluorinated Building Blocks for Organic Synthesis
Motornov V.A., Muzalevskiy V.M., Tabolin A.A., Novikov R.A., Nelyubina Y.V., Nenajdenko V.G., Ioffe S.L.
Journal of Organic Chemistry, 2017
.
Organofluorine chemistry: promising growth areas and challenges
Politanskaya L.V., Selivanova G.A., Panteleeva E.V., Tretyakov E.V., Platonov V.E., Nikul’shin P.V., Vinogradov A.S., Zonov Y.V., Karpov V.M., Mezhenkova T.V., Vasilyev A.V., Koldobskii A.B., Shilova O.S., Morozova S.M., Burgart Y.V., et. al.
Russian Chemical Reviews, 2019
.
Substituted polynorbornenes as promising materials for gas separation membranes
Finkelshtein E.S., Bermeshev M.V., Gringolts M.L., Starannikova L.E., Yampolskii Y.P.
Russian Chemical Reviews, 2011
.
Diels–Alder reaction of β-fluoro-β-nitrostyrenes with cyclic dienes
Ponomarev S.A., Larkovich R.V., Aldoshin A.S., Tabolin A.A., Ioffe S.L., Groß J., Opatz T., Nenajdenko V.G.
Beilstein Journal of Organic Chemistry, 2021
.
The Meinwald rearrangement in tandem processes (microreview)
Mamedova V.L., Khikmatova G.Z.
Chemistry of Heterocyclic Compounds, 2017
.
Peracid Reactions. III.1 The Oxidation of Bicyclo [2.2.1]heptadiene2
Meinwald J., Labana S.S., Chadha M.S.
Journal of the American Chemical Society, 1963
.
Shastin A.V., Muzalevsky V.M., Balenkova E.S., Nenajdenko V.G.
Mendeleev Communications, 2006
.
Versatile Catalytic Reactions of Norbornadiene Derivatives with Alkynes
Khan R., Chen J., Fan B.
Advanced Synthesis and Catalysis, 2020
.
Norbornadiene–quadricyclane — an effective molecular system for the storage of solar energy
Bren' V.A., Dubonosov A.D., Minkin V.I., Chernoivanov V.A.
Russian Chemical Reviews, 1991
.
Do fluorine atoms attached to sp2-hybridized carbon atoms hinder electrophilic addition to the CC bond?
Polishchuk V.R., Mysov E.I., Stankevitch I.V., Chistyakov A.L., Potechin K.A., Struchkov Y.T.
Journal of Fluorine Chemistry, 1993
.
Norbornadiene–quadricyclane as an abiotic system for the storage of solar energy
Dubonosov A.D., Bren V.A., Chernoivanov V.A.
Russian Chemical Reviews, 2002
.
New synthetic approach to α-fluoro-β-arylvinyl sulfones and their application in Diels–Alder reactions
Shastin A.V., Nenajdenko V.G., Muzalevskiy V.M., Balenkova E.S., Fröhlich R., Haufe G.
Tetrahedron, 2008
.
Synthesis and Diels–Alder cycloaddition reaction of norbornadiene and benzonorbornadiene dimers
Nişancı B., Dalkılıç E., Güney M., Daştan A.
Beilstein Journal of Organic Chemistry, 2009