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Regioselective synthesis of 1-azinyl-1′-isopropenylferrocenes

Alexandra Aleksandrovna Musikhina 1, 2
Alexandra Aleksandrovna Musikhina
, 
Irina Aleksandrovna Utepova 1, 2
Irina Aleksandrovna Utepova
, 
Oleg Nikolaevich Chupakhin 1, 2
Oleg Nikolaevich Chupakhin
, 
Anna Isaakovna Suvorova 2
Anna Isaakovna Suvorova
, 
Elena Yur'evna Zyryanova 2
Elena Yur'evna Zyryanova
10.1016/j.mencom.2020.03.026
Published 2020-03-02
Communication , Volume 30, Issue 2, 209-210
4
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Musikhina A. A. et al. Regioselective synthesis of 1-azinyl-1′-isopropenylferrocenes // Mendeleev Communications. 2020. Vol. 30. No. 2. pp. 209-210.
GOST all authors (up to 50) Copy
Musikhina A. A., Utepova I. A., Chupakhin O. N., Suvorova A. I., Zyryanova E. Y. Regioselective synthesis of 1-azinyl-1′-isopropenylferrocenes // Mendeleev Communications. 2020. Vol. 30. No. 2. pp. 209-210.
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TY - JOUR
DO - 10.1016/j.mencom.2020.03.026
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2020.03.026
TI - Regioselective synthesis of 1-azinyl-1′-isopropenylferrocenes
T2 - Mendeleev Communications
AU - Musikhina, Alexandra Aleksandrovna
AU - Utepova, Irina Aleksandrovna
AU - Chupakhin, Oleg Nikolaevich
AU - Suvorova, Anna Isaakovna
AU - Zyryanova, Elena Yur'evna
PY - 2020
DA - 2020/03/02
PB - Mendeleev Communications
SP - 209-210
IS - 2
VL - 30
ER -
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@article{2020_Musikhina,
author = {Alexandra Aleksandrovna Musikhina and Irina Aleksandrovna Utepova and Oleg Nikolaevich Chupakhin and Anna Isaakovna Suvorova and Elena Yur'evna Zyryanova},
title = {Regioselective synthesis of 1-azinyl-1′-isopropenylferrocenes},
journal = {Mendeleev Communications},
year = {2020},
volume = {30},
publisher = {Mendeleev Communications},
month = {Mar},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2020.03.026},
number = {2},
pages = {209--210},
doi = {10.1016/j.mencom.2020.03.026}
}
MLA
Cite this
MLA Copy
Musikhina, Alexandra Aleksandrovna, et al. “Regioselective synthesis of 1-azinyl-1′-isopropenylferrocenes.” Mendeleev Communications, vol. 30, no. 2, Mar. 2020, pp. 209-210. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2020.03.026.

Keywords

azines
ferrocenes
Friedel–Crafts acylation
isopropenylferrocene
regioselective synthesis
Wittig reaction

Abstract

The Friedel–Crafts acetylation (Ac2O/AlCl3) reaction of azinylferrocenes occurs regioselectively at position 1′. Acetylated derivatives upon reaction with Ph3P=CH2 give the corresponding 1-azinyl-1′-isopropenylferrocenes.

References

1.
10.1016/j.mencom.2020.03.026_sbref0005a
Ricci
Ferrocenes: Compounds, Properties and Applications, 2011
2.
10.1016/j.mencom.2020.03.026_sbref0005b
Ferrocenes: Ligands, Materials and Biomolecules, 2008
3.
10.1016/j.mencom.2020.03.026_sbref0005c
Herberhold
Ferrocenes: Homogeneous Catalysis, Materials Science, 1995
4.
Electrochemically Switchable Cucurbit[7]uril-Based Pseudorotaxanes
Sobransingh D., Kaifer A.E.
Organic Letters, 2006
5.
Reversible and Oriented Immobilization of Ferrocene-Modified Proteins
Yang L., Gomez-Casado A., Young J.F., Nguyen H.D., Cabanas-Danés J., Huskens J., Brunsveld L., Jonkheijm P.
Journal of the American Chemical Society, 2012
7.
Supramolecular Velcro for Reversible Underwater Adhesion
Ahn Y., Jang Y., Selvapalam N., Yun G., Kim K.
Angewandte Chemie - International Edition, 2013
8.
Redox-switchable supramolecular polymers for responsive self-healing nanofibers in water
Yan Q., Feng A., Zhang H., Yin Y., Yuan J.
Polymer Chemistry, 2013
10.
Poly(ferrocenylsilane) Gels and Hydrogels with Redox-Controlled Actuation
Hempenius M.A., Cirmi C., Savio F.L., Song J., Vancso G.J.
Macromolecular Rapid Communications, 2010
11.
Redox-responsive self-healing materials formed from host–guest polymers
Nakahata M., Takashima Y., Yamaguchi H., Harada A.
Nature Communications, 2011
12.
Multistimuli Responsive and Electroactive Supramolecular Gels Based on Ionic Liquid Gemini Guest
Yuan C., Guo J., Tan M., Guo M., Qiu L., Yan F.
ACS Macro Letters, 2014
13.
Reversible formation and disruption of micelles by control of the redox state of the head group
Saji T., Hoshino K., Aoyagui S.
Journal of the American Chemical Society, 1985
14.
Chemical oxidation of a redox-active, ferrocene-containing cationic lipid: influence on interactions with DNA and characterization in the context of cell transfection.
Aytar B.S., Muller J.P., Golan S., Kondo Y., Talmon Y., Abbott N.L., Lynn D.M.
Journal of Colloid and Interface Science, 2012
15.
Redox-Based Control of the Transformation and Activation of siRNA Complexes in Extracellular Environments Using Ferrocenyl Lipids
Aytar B.S., Muller J.P., Kondo Y., Talmon Y., Abbott N.L., Lynn D.M.
Journal of the American Chemical Society, 2013
16.
Redox Control within Single-Site Polymerization Catalysts
Gregson C.K., Gibson V.C., Long N.J., Marshall E.L., Oxford P.J., White A.J.
Journal of the American Chemical Society, 2006
19.
Redox Control of Group 4 Metal Ring-Opening Polymerization Activity toward l-Lactide and ε-Caprolactone
Wang X., Thevenon A., Brosmer J.L., Yu I., Khan S.I., Mehrkhodavandi P., Diaconescu P.L.
Journal of the American Chemical Society, 2014
20.
Redox control of a dendritic ferrocenyl-based homogeneous catalyst.
Neumann P., Dib H., Caminade A., Hey‐Hawkins E.
Angewandte Chemie - International Edition, 2014
21.
Redox Tuning of a Direct Asymmetric Aldol Reaction
Zhang Q., Cui X., Zhang L., Luo S., Wang H., Wu Y.
Angewandte Chemie - International Edition, 2015
22.
A ferrocenylspiropyran that functions as a molecular photomemory with controllable depth.
Nagashima S., Murata M., Nishihara H.
Angewandte Chemie - International Edition, 2006
24.
Photophysics and transient nonlinear optical response of donor–[60]fullerene hybrids
Aloukos P., Iliopoulos K., Couris S., Guldi D.M., Sooambar C., Mateo-Alonso A., Nagaswaran P.G., Bonifazi D., Prato M.
Journal of Materials Chemistry A, 2011
28.
10.1016/j.mencom.2020.03.026_sbref0050b
Synthetic Metal-Containing Polymers, 2004
29.
10.1016/j.mencom.2020.03.026_sbref0050c
Long
Ferrocenes: Ligands, Materials and Biomolecules, 2008
30.
Patchy Nanocapsules of Poly(vinylferrocene)-Based Block Copolymers for Redox-Responsive Release
Staff R.H., Gallei M., Mazurowski M., Rehahn M., Berger R., Landfester K., Crespy D.
ACS Nano, 2012
31.
Reversible Activity Modulation of Surface-Attached Grubbs Second Generation Type Catalysts Using Redox-Responsive Polymers
Elbert J., Mersini J., Vilbrandt N., Lederle C., Kraska M., Gallei M., Stühn B., Plenio H., Rehahn M.
Macromolecules, 2013
32.
Polymer‐Modified Mesoporous Silica Thin Films for Redox‐Mediated Selective Membrane Gating
Elbert J., Krohm F., Rüttiger C., Kienle S., Didzoleit H., Balzer B.N., Hugel T., Stühn B., Gallei M., Brunsen A.
Advanced Functional Materials, 2013
33.
Direct C–C Coupling of Ferrocenyllithium and Azaheterocycles by Nucleophilic Substitution of Hydrogen – Synthesis of Mono- and 1,1′-Diazinylferrocenes
Chupakhin O.N., Utepova I.A., Kovalev I.S., Rusinov V.L., Starikova Z.A.
European Journal of Organic Chemistry, 2007
34.
Stable σH-adducts in reactions of ferrocenyllithium with azines
Utepova I.A., Lakhina A.E., Varaksin M.V., Kovalev I.S., Rusinov V.L., Slepukhin P.A., Kodess M.I., Chupakhin O.N.
Russian Chemical Bulletin, 2008
36.
Polyvinylferrocene-Based Amphiphilic Block Copolymers Featuring Functional Junction Points for Cross-Linked Micelles
Morsbach J., Elbert J., Rüttiger C., Winzen S., Frey H., Gallei M.
Macromolecules, 2016
37.
Synthesis and Antifungal Activity of 3-substituted 5-ferrocenyl-1H-pyrazoles
Ge M., Huang H., Gou X., Hua C., Chen B., Zhao J.
Chemistry of Heterocyclic Compounds, 2018
39.
Multi-functionalized ferrocenes: –Synthesis and characterization –
Hildebrandt A., Al Khalyfeh K., Schaarschmidt D., Korb M.
Journal of Organometallic Chemistry, 2016
40.
901. Ferrocene derivatives. Part IX. Some disubstituted derivatives
Osgerby J.M., Pauson P.L.
Journal of the Chemical Society (Resumed), 1961
41.
Ferrocenyl Quinone Methide-Thiol Adducts as New Antiproliferative Agents: Synthesis, Metabolic Formation from Ferrociphenols, and Oxidative Transformation
Wang Y., Richard M., Top S., Dansette P.M., Pigeon P., Vessières A., Mansuy D., Jaouen G.
Angewandte Chemie - International Edition, 2016
42.
Synthesis, Cytotoxicity, and COMPARE Analysis of Ferrocene and [3]Ferrocenophane Tetrasubstituted Olefin Derivatives against Human Cancer Cells
Görmen M., Pigeon P., Top S., Hillard E.A., Huché M., Hartinger C.G., de Montigny F., Plamont M., Vessières A., Jaouen G.
ChemMedChem, 2010
43.
Synthesis of vinylferrocene and the ligand-exchange reaction between its copolymer and carbon nanotubes
Shi R., Wang H., Tang P., Bin Y.
Frontiers of Chemical Science and Engineering, 2014
44.
A Practical Three-Step Synthesis of Vinylferrocene
Šebesta R., Plevová K., Mudráková B.
Synthesis, 2017
45.
Effect of heterocyclic derivatives of ferrocene on free-radical polymerization of methyl methacrylate and styrene
Islamova R.M., Golovochesova O.I., Monakov Y.B., Utepova I.A., Musikhina A.A., Chupakhin O.N.
Polymer Science - Series B, 2010
46.
Complex radical polymerization of methyl methacrylate in the presence of heterocyclic ferrocene derivatives
Monakov Y.B., Islamova R.M., Golovochesova O.I., Utepova I.A., Musikhina A.A., Chupakhin O.N.
Doklady Chemistry, 2010