Articles de revues : « Halonium ions »

1

KOSER, G. F. « ChemInform Abstract : Halonium Ions ». ChemInform 28, n^o 9 (4 août 2010) : no. http://dx.doi.org/10.1002/chin.199709284.

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2

Ohta, Brian K. « The structure of halonium ions in superacidic solutions ». Pure and Applied Chemistry 85, n^o 10 (1 octobre 2013) : 1959–65. http://dx.doi.org/10.1351/pac-con-13-04-06.

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Isotopic perturbation of equilibrium was applied to 1,2-bridged halonium ions to determine whether they exist as single symmetric structures or as a rapid equilibrium of asymmetric structures. The observed deuterium isotope shifts are qualitatively and quantitatively consistent with the presence of intrinsic and equilibrium isotope shifts. The presence of equilibrium shifts suggests that these ions exist as a rapid equilibrium of asymmetric structures. Though the asymmetric structures were initially ascribed to β-halocarbenium ions, subsequent computational data suggest that 1,2-bridged halonium ions react with sulfur dioxide (SO2), the experimental solvent. Our current hypothesis is that the equilibrium isotope shifts result from rapid labile addition of SO2 to the halonium ions. Other hypotheses have been invoked to explain the results and are considered in the context of the available data.

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3

Turunen, Lotta, et Máté Erdélyi. « Halogen bonds of halonium ions ». Chemical Society Reviews 49, n^o 9 (2020) : 2688–700. http://dx.doi.org/10.1039/d0cs00034e.

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4

Holman, Robert W., Jennifer Davis, Amy Walstrom, Michelle McCombs, Gina Jackson, Shannon Sullivan et Michael L. Gross. « An Investigation of Gaseous α-Halogenated Carbocations and Isomeric Halonium, Halenium, and Allylhalonium Ions ». Australian Journal of Chemistry 56, n^o 5 (2003) : 437. http://dx.doi.org/10.1071/ch02264.

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We investigated with tandem mass spectrometric methods (MS/MS) the nature and extent of stabilization of gas-phase alkyl, vinyl and 2-allyl carbenium ions caused by halogen participation of neighboring chlorine and bromine atoms. The extent of halogen atom stabilization is greatest for alkyl ions, followed closely by that for vinyl ions, and is significantly less for the 2-halosubstituted allyl ions. The data is consistent with bridged halonium ion formation in alkyl systems and bridged halenium ion formation in vinyl systems. Our results for the 2-chloro allyl system are in accord with an earlier NMR interpretation rather than with recent theory, indicating that a bridged allyl halonium ion species is involved.

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Lindblad, Sofia, Flóra Boróka Németh, Tamás Földes, Alan Vanderkooy, Imre Pápai et Máté Erdélyi. « O–I–O halogen bond of halonium ions ». Chemical Communications 56, n^o 67 (2020) : 9671–74. http://dx.doi.org/10.1039/d0cc03513k.

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6

Struble, Mark D., Michael T. Scerba, Maxime Siegler et Thomas Lectka. « Evidence for a Symmetrical Fluoronium Ion in Solution ». Science 340, n^o 6128 (4 avril 2013) : 57–60. http://dx.doi.org/10.1126/science.1231247.

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Halonium ions, in which formally positively charged halogens (chlorine, bromine, and iodine) are equivalently attached to two carbon atoms through three-center bonds, are well established in the synthetic chemistry of organochlorides, bromides, and iodides. Mechanistic studies of these ions have generated numerous insights into the origins of stereoselectivity in addition and displacement reactions. However, it has not been clear whether fluorine can form a halonium ion in the same manner. We present chemical and theoretical evidence for the transient generation of a true symmetrical fluoronium ion in solution from an appropriately configured precursor.

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7

Haubenstock, Howard, et Ronald R. Sauers. « Computational studies of vinyl-stabilized halonium ions ». Tetrahedron 60, n^o 5 (janvier 2004) : 1191–96. http://dx.doi.org/10.1016/j.tet.2003.11.073.

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8

Haubenstock, Howard, et Ronald R. Sauers. « Computational studies of benzyl-substituted halonium ions ». Tetrahedron 61, n^o 35 (août 2005) : 8358–65. http://dx.doi.org/10.1016/j.tet.2005.06.091.

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9

Hennecke, Ulrich, Christian H. Müller et Roland Fröhlich. « Enantioselective Haloetherification by Asymmetric Opening ofmeso-Halonium Ions ». Organic Letters 13, n^o 5 (4 mars 2011) : 860–63. http://dx.doi.org/10.1021/ol1028805.

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10

Hollis, Jane, John M. Tedder et G. Stewart Walker. « Investigations of halonium ions in the gas phase ». Journal of the Chemical Society, Perkin Transactions 2, n^o 8 (1991) : 1187. http://dx.doi.org/10.1039/p29910001187.

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11

Olah, George A., Hans Doggweiler, Jeff D. Felberg et Stephan Frohlich. « Onium ions. 33. (Trimethylsilyl)- and [(trimethylsilyl)methyl]oxonium and halonium ions ». Journal of Organic Chemistry 50, n^o 24 (novembre 1985) : 4847–51. http://dx.doi.org/10.1021/jo00224a039.

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12

Suzaki, Yuji, Takashi Saito, Tomohito Ide et Kohtaro Osakada. « A rhomboid-shaped organic host molecule with small binding space. Unsymmetrical and symmetrical inclusion of halonium ions ». Dalton Trans. 43, n^o 18 (2014) : 6643–49. http://dx.doi.org/10.1039/c3dt53629g.

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13

Damrauer, Robert, Michael D. Leavell et Christopher M. Hadad. « Computational Studies of Halonium Ions of Cyclohexene and Cyclopentene ». Journal of Organic Chemistry 63, n^o 25 (décembre 1998) : 9476–85. http://dx.doi.org/10.1021/jo981660d.

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14

Schneider, Tobias F., et Daniel B. Werz. « The Quest for Tetracoordinated Halonium Ions : A Theoretical Investigation ». Organic Letters 12, n^o 21 (5 novembre 2010) : 4844–47. http://dx.doi.org/10.1021/ol102059b.

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15

Grossman, Robert B., et Robert J. Trupp. « The first reagent-controlled asymmetric halolactonizations. Dihydroquinidine-halogen complexes as chiral sources of positive halogen ion ». Canadian Journal of Chemistry 76, n^o 9 (1 septembre 1998) : 1233–37. http://dx.doi.org/10.1139/v98-153.

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The first reagent-controlled asymmetric halolactonizations are described. Complexes of I+ with O-acyl- and O-aryldihydroquinidines are used to promote the asymmetric halolactonization of prochiral θ, δ-unsaturated carboxylic acids with low but measurable and reproducible enantioselectivity. Experimental factors affecting the ee's are described. Key words: halocyclization, halogenation, halonium ions, chiral, stereoselective.

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16

Zunino, Fabien, Fei Liu, Christian Berrier, Agnès Martin-Mingot, Sébastien Thibaudeau, Marie-Paule Jouannetaud, Jean-Claude Jacquesy et Christian Bachmann. « Gem-difluorination in superacid : The dramatic role of halonium ions ». Journal of Fluorine Chemistry 129, n^o 9 (septembre 2008) : 775–80. http://dx.doi.org/10.1016/j.jfluchem.2008.06.020.

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17

Remete, Attila Márió, Tamás T. Novák, Melinda Nonn, Matti Haukka, Ferenc Fülöp et Loránd Kiss. « Synthesis of novel fluorinated building blocks via halofluorination and related reactions ». Beilstein Journal of Organic Chemistry 16 (16 octobre 2020) : 2562–75. http://dx.doi.org/10.3762/bjoc.16.208.

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A study exploring halofluorination and fluoroselenation of some cyclic olefins, such as diesters, imides, and lactams with varied functionalization patterns and different structural architectures is described. The synthetic methodologies were based on electrophilic activation through halonium ions of the ring olefin bonds, followed by nucleophilic fluorination with Deoxo-Fluor®. The fluorine-containing products thus obtained were subjected to elimination reactions, yielding various fluorine-containing small-molecular entities.

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18

Gaude, Didier, Gisèle Gellon, Raymond Le Goaller et Jean-Louis Pierre. « Influence de la complexation sur la réactivité de nitrates d'halogènes ». Canadian Journal of Chemistry 67, n^o 1 (1 janvier 1989) : 104–8. http://dx.doi.org/10.1139/v89-018.

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Iodine nitrate or bromine nitrate in acetonitrile or in chloroform react with a variety of phenolic substrates to form both halogenated and nitrated products. In the presence of strong complexing agents of halonium ions, no reaction occurs, while in the presence of pyridine or triethylamine, only halogenated phenols exhibiting a strong ortho-directing effect of the phenolic function are produced. Keywords: phenols, iodine nitrate, bromine nitrate, halogenation, nitration.

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19

Hennecke, Ulrich, Christian H. Mueller et Roland Froehlich. « ChemInform Abstract : Enantioselective Haloetherification by Asymmetric Opening of meso-Halonium Ions. » ChemInform 42, n^o 23 (12 mai 2011) : no. http://dx.doi.org/10.1002/chin.201123089.

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20

Biswas, Mukul, et Joseph P. Kennedy. « Cationic polymerization by cyclic halonium ions I. The 2,5-dimethylhexane/Bcl3 /isobutylene system ». Makromolekulare Chemie. Macromolecular Symposia 3, n^o 1 (juin 1986) : 113–27. http://dx.doi.org/10.1002/masy.19860030110.

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21

Silverberg, Lee Jonathan, Kurt Andrew Kistler, Kyle Brobst, Hemant Prabhakar Yennawar, Anthony Lagalante, Gang He, Khalid Ali et al. « Reactions of the halonium ions of carenes and pinenes : An experimental and theoretical study ». European Journal of Chemistry 6, n^o 4 (31 décembre 2015) : 430–43. http://dx.doi.org/10.5155/eurjchem.6.4.430-443.1307.

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22

Sharma, Dilip K. Sen, Sarah Meza de Hoejer et Paul Kebarle. « Stabilities of halonium ions from a study of gas-phase equilibria R+ + XR' = (RXR')+ ». Journal of the American Chemical Society 107, n^o 13 (juin 1985) : 3757–62. http://dx.doi.org/10.1021/ja00299a002.

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23

Yamabe, Shinichi, Tsutomu Minato, Masahiro Seki et Satoshi Inagaki. « Zigzag collapse of four-membered rings generated by additions of halonium ions to cyclopropanes ». Journal of the American Chemical Society 110, n^o 18 (août 1988) : 6047–53. http://dx.doi.org/10.1021/ja00226a019.

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24

Lehmann, Mathias, Axel Schulz et Alexander Villinger. « Bissilylated Halonium Ions : [Me3SiXSiMe3][B(C6F5)4] (X=F, Cl, Br, I) ». Angewandte Chemie International Edition 48, n^o 40 (21 septembre 2009) : 7444–47. http://dx.doi.org/10.1002/anie.200902992.

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25

Sethio, Daniel, Gerardo Raggi, Roland Lindh et Máté Erdélyi. « Halogen Bond of Halonium Ions : Benchmarking DFT Methods for the Description of NMR Chemical Shifts ». Journal of Chemical Theory and Computation 16, n^o 12 (2 novembre 2020) : 7690–701. http://dx.doi.org/10.1021/acs.jctc.0c00860.

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26

Stoyanov, Evgenii S. « Chemical Properties of Dialkyl Halonium Ions (R2Hal+) and Their Neutral Analogues, Methyl Carboranes, CH3–(CHB11Hal11), Where Hal = F, Cl ». Journal of Physical Chemistry A 121, n^o 15 (6 avril 2017) : 2918–23. http://dx.doi.org/10.1021/acs.jpca.7b01203.

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27

Kalescky, Robert, Wenli Zou, Elfi Kraka et Dieter Cremer. « Quantitative Assessment of the Multiplicity of Carbon–Halogen Bonds : Carbenium and Halonium Ions with F, Cl, Br, and I ». Journal of Physical Chemistry A 118, n^o 10 (4 mars 2014) : 1948–63. http://dx.doi.org/10.1021/jp4120628.

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28

Angelini, Giancarlo, Gaetano Lilla et Maurizio Speranza. « Gas-phase base-induced elimination reactions in onium intermediates. 2. Stereochemistry and orientation in alkene formation from gaseous halonium ions ». Journal of the American Chemical Society 111, n^o 19 (septembre 1989) : 7393–99. http://dx.doi.org/10.1021/ja00201a017.

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29

Shellhamer, Dale F., Jeannette L. Allen, Rachel D. Allen, David C. Gleason, Colleen O'Neil Schlosser, Benjamin J. Powers, John W. Probst et al. « Ionic Reaction of Halogens with Terminal Alkenes : The Effect of Electron-Withdrawing Fluorine Substituents on the Bonding of Halonium Ions ». Journal of Organic Chemistry 68, n^o 10 (mai 2003) : 3932–37. http://dx.doi.org/10.1021/jo030030v.

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30

Neverov, Alexei A., Theresa L. Muise et R. S. Brown. « X+ transfer from the halonium ions of adamantylideneadamantane to acceptor olefins. The possibility of chiral induction in the transfer process ». Canadian Journal of Chemistry 75, n^o 12 (1 décembre 1997) : 1844–50. http://dx.doi.org/10.1139/v97-617.

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The bromonium ion of adamantylideneadamantane (Ad=Ad-Br+) has been used to induce the bromocyclization of a 4-pentenyl glycoside (10) and a 5-hexenyl glycoside (11) in dichloroethane. The kinetics of these processes have been studied at 25 °C in the presence of varying [Ad=Ad] and, in the case of the transfer to 10, in the presence of pentanol. The second-order rate constants for bromocyclization of these two alkenes are (1.04 ± 0.06) × 10−1 M−1 s−1 and (5.34 ± 0.2) × 10−1 M−1 s−1, respectively, and in no case does added Ad=Ad or pentanol alter the reaction rate. The kinetic behavior is interpreted in terms of cyclization occurring directly from a 1:1 complex of Ad=Ad-Br+ and 10 or 11. The chiral induction for the bromocyclization of 10 promoted by AdAd-Br+ was measured at 20% e.e., the (−)-(S)-tetrahydrofurfuryl bromide being the dominant stereoisomer. Ad=Ad molecules substituted at one of the homoallylic carbons by an axial methyl group (12), or by two methyl groups (axial and equatorial), were synthesized and the 1H NMR spectra of their bromonium ions is given. These materials are not stable for prolonged times at room temperature. A limited kinetic study of the reaction of 12-Br+ and 4-pentenol indicated that the Br+ transfer is 500 times faster than the comparable transfer from Ad=Ad-Br+ to 4-pentenol. The possibility of using these materials to induce chiral bromocyclization is discussed. Keywords: bromonium ion, halonium, transfer, chiral, adamantylideneadamantane.

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31

Budanow, Alexandra, Tanja Sinke, Jan Tillmann, Michael Bolte, Matthias Wagner et Hans-Wolfram Lerner. « Two-Coordinate Gallium Ion [tBu3Si-Ga-SitBu3]+and the Halonium Ions [tBu3Si-X-SitBu3]+(X = Br, I) : Sources of the Supersilyl Cation [tBu3Si]+ ». Organometallics 31, n^o 20 (27 septembre 2012) : 7298–301. http://dx.doi.org/10.1021/om300854e.

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32

Neverov, A. A., et R. S. Brown. « Br+and I+Transfer from the Halonium Ions of Adamantylideneadamantane to Acceptor Olefins. Halocyclization of 1,ω-Alkenols and Alkenoic Acids Proceeds via Reversibly Formed Intermediates ». Journal of Organic Chemistry 61, n^o 3 (janvier 1996) : 962–68. http://dx.doi.org/10.1021/jo951703f.

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33

Okazaki, Takao, et Kenneth K. Laali. « Intermediates of Halogen Addition to Phenylethynes and Protonation of Phenylethynyl Halides. Open Halovinyl Cations, Bridged Halonium, or Phenyl-Bridged Ions : A Substituent Effect Study by DFT and GIAO-DFT ». Journal of Organic Chemistry 71, n^o 26 (décembre 2006) : 9643–50. http://dx.doi.org/10.1021/jo061632s.

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34

Williams, Ian H. « Preface ». Pure and Applied Chemistry 85, n^o 10 (1 octobre 2013) : iv. http://dx.doi.org/10.1351/pac20138510iv.

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The IUPAC Conference on Physical Organic Chemistry (ICPOC) series of biennial conferences has a long history as the leading international meeting on physical organic chemistry. From its first installment in Crans sur Sierre (Switzerland) in 1972, ICPOC has acted as a focus point for the physical organic community worldwide, and the conference series enjoys a respected international reputation. With its focus on relating chemical behavior and properties to molecular structure through the development of (ideally quantitative) understanding of structure–property relationships, physical organic chemistry (POC) finds wide application in tackling current scientific challenges and has been undergoing something of a resurgence in recent years. ICPOC-21, held on 9-13 September 2012 at the University of Durham, UK, provided a forum for researchers (329 delegates from 38 countries) in academia and industry, and at all career stages, to present their results to the POC community and to exchange ideas, meet old friends, and make new contacts while enjoying spectacular views of the World Heritage castle and cathedral. In line with a developing interpretation of POC as a widely applicable approach to chemistry, the scientific program embraced three broad themes (physical underpinnings, mechanism and catalysis, and supramolecular chemistry) but often these strands were as inseparably interconnected as the three leaves held in unity in the minimal saddle trefoil adopted as the conference logo. The scope of the meeting is illustrated by the selection of contributions included in this issue of Pure and Applied Chemistry. In addition to the 24 plenary and keynote lectures, there were 120 contributed talks and 141 poster presentations. Donna Blackmond's paper on the interplay of thermodynamics and kinetics in dictating organocatalytic reactivity and selectivity demonstrates the use of kinetic modeling to provide mechanistic understanding leading to practical application. Martin Tanner's discussion of rearrangements catalyzed by indole alkaloid prenyltransferases shows how the experimental POC approach may shed light on enzyme mechanisms, while Dean Tantillo describes the application of quantum chemical dynamics calculations to mechanistic problems in the field of terpene biosynthesis, and a blend of experiment and computation is presented in Brian Ohta's account of the structure of halonium ions in superacidic solutions. Hiromitsu Maeda reviews research on various stimuli-responsive circularly polarized luminescence properties derived from π-conjugated molecules and related materials, and Jason Harper summarizes progress towards a predictive understanding of how ionic solvents affect and control organic reactivity. Finally, Izumi Iwakura reports directly observations of the Claisen rearrangement by timeresolved vibrational spectroscopy using a few-optical-cycle pulse laser. This selection of excellent work provides only a taste, but the conference as a whole showed that the international POC community is as vital and vibrant as it has ever been, promising exciting times ahead for this approach to chemistry. The next ICPOC will be held in Ottawa (Canada) 10-15 August 2014 under the chairmanship of Prof. Paul Mayer (University of Ottawa). Further information can be found at http://events.science.uottawa. ca/icpoc22/welcome.html.Ian H. Williams Conference Chair and Editor

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35

OLAH, G. A., H. DOGGWEILER, J. D. FELBERG et S. FROHLICH. « ChemInform Abstract : Onium Ions. Part 33. (Trimethylsilyl)- and [(Trimethylsilyl)methyl]oxonium and -halonium Ions. » Chemischer Informationsdienst 17, n^o 19 (13 mai 1986). http://dx.doi.org/10.1002/chin.198619161.

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36

Zunino, Fabien, Fei Liu, Christian Berrier, Agnes Martin-Mingot, Sebastien Thibaudeau, Marie-Paule Jouannetaud, Jean-Claude Jacquesy et Christian Bachmann. « ChemInform Abstract : gem-Difluorination in Superacid : The Dramatic Role of Halonium Ions. » ChemInform 40, n^o 4 (27 janvier 2009). http://dx.doi.org/10.1002/chin.200904034.

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37

YAMABE, S., T. MINATO, M. SEKI et S. INAGAKI. « ChemInform Abstract : Zigzag Collapse of Four-Membered Rings Generated by Additions of Halonium Ions to Cyclopropanes. » ChemInform 19, n^o 51 (20 décembre 1988). http://dx.doi.org/10.1002/chin.198851084.

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38

SEN SHARMA, D. K., S. MEZA DE HOEJER et P. KEBARLE. « ChemInform Abstract : Stabilities of Halonium Ions from a Study of Gas-Phase Equilibria R++ XR′ = (RXR′)+ ». Chemischer Informationsdienst 16, n^o 42 (22 octobre 1985). http://dx.doi.org/10.1002/chin.198542114.

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39

Hoffmann, Kurt F., Anja Wiesner, Carsten Müller, Simon Steinhauer, Helmut Beckers, Muhammad Kazim, Cody Ross Pitts, Thomas Lectka et Sebastian Riedel. « Structural proof of a [C–F–C]+ fluoronium cation ». Nature Communications 12, n^o 1 (6 septembre 2021). http://dx.doi.org/10.1038/s41467-021-25592-6.

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AbstractOrganic fluoronium ions can be described as positively charged molecules in which the most electronegative and least polarizable element fluorine engages in two partially covalent bonding interactions to two carbon centers. While recent solvolysis experiments and NMR spectroscopic studies on a metastable [C–F–C]+ fluoronium ion strongly support the divalent fluoronium structure over the alternative rapidly equilibrating classical carbocation, the model system has, to date, eluded crystallographic analysis to confirm this phenomenon in the solid state. Herein, we report the single crystal structure of a symmetrical [C–F–C]+ fluoronium cation. Besides its synthesis and crystallographic characterization as the [Sb2F11]− salt, vibrational spectra are discussed and a detailed analysis concerning the nature of the bonding situation in this fluoronium ion and its heavier halonium homologues is performed, which provides detailed insights on this molecular structure.

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40

ANGELINI, G., G. LILLA et M. SPERANZA. « ChemInform Abstract : Gas-Phase Base-Induced Elimination Reactions in Onium Intermediates. Part 2. Stereochemistry and Orientation in Alkene Formation from Gaseous Halonium Ions. » ChemInform 21, n^o 2 (9 janvier 1990). http://dx.doi.org/10.1002/chin.199002102.

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