Conformational preferences of α-fluoroketones may influence their reactivity

Scholarly Works

• Ryan, P.; Iftikhar, R.; Hunter, L. Origami with small molecules: exploiting the C-F bond as a conformational tool. Beilstein journal of organic chemistry 2025, 21, 680–716. doi:10.3762/bjoc.21.54
• Francisco, C. B.; Dourado, F. F.; Fernandes, C. d. S.; Gauze, G. d. F.; Basso, E. A. The role of intra and intermolecular interactions on the conformational dynamics of 2-halo-1-phenylpropanols: Structure and solvent effects. Journal of Molecular Structure 2025, 1322, 140493. doi:10.1016/j.molstruc.2024.140493
• Francisco, C. B.; Fernandes, C. d. S.; Franco Dourado, F.; Gauze, G. d. F.; Rittner, R.; Prosser, R. S.; Basso, E. A. Conformational Landscape of α-Halopropiophenones Determined by nJC-H NMR Reveals Unexpected Patterns and Geometric Constraints. The journal of physical chemistry. A 2024, 128, 1566–1575. doi:10.1021/acs.jpca.3c06934
• Levine, D. S.; Jacobson, L. D.; Bochevarov, A. D. Large Computational Survey of Intrinsic Reactivity of Aromatic Carbon Atoms with Respect to a Model Aldehyde Oxidase. Journal of chemical theory and computation 2023, 19, 9302–9317. doi:10.1021/acs.jctc.3c00913
• YILDIRIM, M. H.; ÖZEK YILDIRIM, A. m- ve p-nitro Bromoasetofenon Bileşiklerinin Deneysel (FT‒IR, NMR) ve Teorik Yaklaşımlarla Yapılarının Belirlenmesi. Iğdır Üniversitesi Fen Bilimleri Enstitüsü Dergisi 2023, 13, 1663–1675. doi:10.21597/jist.1280807
• Rodrigues Silva, D.; Zeoly, L. A.; Vermeeren, P.; Cormanich, R. A.; Hamlin, T. A.; Fonseca Guerra, C.; Freitas, M. P. Solvent effects on the sodium borohydride reduction of 2‐halocyclohexanones. Journal of Physical Organic Chemistry 2023, 36. doi:10.1002/poc.4556
• Silva, D. R.; de Azevedo Santos, L.; Hamlin, T. A.; Bickelhaupt, F. M.; Freitas, M. P.; Guerra, C. F. Dipolar repulsion in α-halocarbonyl compounds revisited. Physical chemistry chemical physics : PCCP 2021, 23, 20883–20891. doi:10.1039/d1cp02502c
• Le, V.-D.; Dang, C.-H.; Nguyen, C.-H.; Nguyen, H.-U.; Nguyen, T.-D. Synthesis of β-Methyl Alcohols: Influence of Alkyl Chain Length on Diastereoselectivity and New Attractants of Rhynchophorus ferrugineus. Journal of agricultural and food chemistry 2021, 69, 5882–5886. doi:10.1021/acs.jafc.1c01875
• Bartolo, N. D.; Demkiw, K. M.; Valentín, E. M.; Hu, C. T.; Arabi, A. A.; Woerpel, K. A. Diastereoselective Additions of Allylmagnesium Reagents to α-Substituted Ketones When Stereochemical Models Cannot Be Used. The Journal of organic chemistry 2021, 86, 7203–7217. doi:10.1021/acs.joc.1c00553
• Zafrani, Y.; Parvari, G.; Amir, D.; Ghindes-Azaria, L.; Elias, S.; Pevzner, A.; Fridkin, G.; Berliner, A.; Gershonov, E.; Eichen, Y.; Saphier, S.; Katalan, S. Modulation of the H-Bond Basicity of Functional Groups by α-Fluorine-Containing Functions and its Implications for Lipophilicity and Bioisosterism. Journal of medicinal chemistry 2021, 64, 4516–4531. doi:10.1021/acs.jmedchem.0c01868
• Citarella, A.; Gentile, D.; Rescifina, A.; Piperno, A.; Mognetti, B.; Gribaudo, G.; Sciortino, M. T.; Holzer, W.; Pace, V.; Micale, N. Pseudo-Dipeptide Bearing α,α-Difluoromethyl Ketone Moiety as Electrophilic Warhead with Activity against Coronaviruses. International journal of molecular sciences 2021, 22, 1398. doi:10.3390/ijms22031398
• Neufeld, J.; Daniliuc, C. G.; Gilmour, R. Fluorohydration of alkynes via I(I)/I(III) catalysis. Beilstein journal of organic chemistry 2020, 16, 1627–1635. doi:10.3762/bjoc.16.135
• Silva, D. R.; Zeoly, L. A.; Cormanich, R. A.; Guerra, C. F.; Freitas, M. P. Evaluation of the Alicyclic Gauche Effect in 2-Fluorocyclohexanone Analogs: a Combined NMR and DFT Study. European Journal of Organic Chemistry 2020, 2020, 884–890. doi:10.1002/ejoc.201901815
• Bartolo, N. D.; Read, J. A.; Valentín, E. M.; Woerpel, K. A. Reactions of Allylmagnesium Reagents with Carbonyl Compounds and Compounds with C═N Double Bonds: Their Diastereoselectivities Generally Cannot Be Analyzed Using the Felkin-Anh and Chelation-Control Models. Chemical reviews 2020, 120, 1513–1619. doi:10.1021/acs.chemrev.9b00414
• Díaz, N.; Jiménez-Grávalos, F.; Suárez, D.; Francisco, E.; Martín-Pendás, Á. Fluorine conformational effects characterized by energy decomposition analysis. Physical chemistry chemical physics : PCCP 2019, 21, 25258–25275. doi:10.1039/c9cp05009d
• Junqing, L.; Han, J.; Jingjing, W.; Pingjie, W.; Jian, H.; Hu, F.; Wu, F. Nickel-Catalyzed Coupling Reaction of α-Bromo-α-fluoroketones with Arylboronic Acids toward the Synthesis of α-Fluoroketones. Organic letters 2019, 21, 6844–6849. doi:10.1021/acs.orglett.9b02474
• de Rezende, F. M.; Freitas, M. P.; Ramalho, T. C. The Perlin effect in 2-halocyclohexanones and 2-halocyclohexanethiones. Computational and Theoretical Chemistry 2019, 1152, 28–31. doi:10.1016/j.comptc.2019.02.011
• Andrade, L. A. F.; Silla, J. M.; Freitas, M. P. An anomalous effect of fluorine on the conformational equilibrium of 2-fluorocyclohexane-1,3-dione. Tetrahedron Letters 2019, 60, 355–357. doi:10.1016/j.tetlet.2018.12.055
• Pattison, G. Methods for the Synthesis of α,α-Difluoroketones. European Journal of Organic Chemistry 2018, 2018, 3520–3540. doi:10.1002/ejoc.201800532

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