ACS Publications. Most Trusted. Most Cited. Most Read
My Activity
CONTENT TYPES

Figure 1Loading Img

The Effect of the Carbonyl and Related Groups on the Reactivity of Halides in SN2 Reactions

Cite this: J. Am. Chem. Soc. 1964, 86, 21, 4645–4650
Publication Date (Print):November 1, 1964
https://doi.org/10.1021/ja01075a025
    ACS Legacy Archive

    Article Views

    3402

    Altmetric

    -

    Citations

    169
    LEARN ABOUT THESE METRICS
    Other access options

    Note: In lieu of an abstract, this is the article's first page.

    Free first page

    Read this article

    To access this article, please review the available access options below.

    Get instant access

    Purchase Access

    Read this article for 48 hours. Check out below using your ACS ID or as a guest.

    Recommended

    Access through Your Institution

    You may have access to this article through your institution.

    Your institution does not have access to this content. You can change your affiliated institution below.

    Cited By

    This article is cited by 169 publications.

    1. Kler Huonnic, Bruno Linclau. The Synthesis and Glycoside Formation of Polyfluorinated Carbohydrates. Chemical Reviews 2022, 122 (20) , 15503-15602. https://doi.org/10.1021/acs.chemrev.2c00086
    2. Benjamin Jeffries, Zhong Wang, Hannah R. Felstead, Jean-Yves Le Questel, James S. Scott, Elisabetta Chiarparin, Jérôme Graton, Bruno Linclau. Systematic Investigation of Lipophilicity Modulation by Aliphatic Fluorination Motifs. Journal of Medicinal Chemistry 2020, 63 (3) , 1002-1031. https://doi.org/10.1021/acs.jmedchem.9b01172
    3. Benjamin Jeffries, Zhong Wang, Jérôme Graton, Simon D. Holland, Thomasin Brind, Ryan D. R. Greenwood, Jean-Yves Le Questel, James S. Scott, Elisabetta Chiarparin, Bruno Linclau. Reducing the Lipophilicity of Perfluoroalkyl Groups by CF2–F/CF2–Me or CF3/CH3 Exchange. Journal of Medicinal Chemistry 2018, 61 (23) , 10602-10618. https://doi.org/10.1021/acs.jmedchem.8b01222
    4. Aniekan Okon, JingJing Han, Surendra Dawadi, Christos Demosthenous, Courtney C. Aldrich, Mamta Gupta, and Carston R. Wagner . Anchimerically Activated ProTides as Inhibitors of Cap-Dependent Translation and Inducers of Chemosensitization in Mantle Cell Lymphoma. Journal of Medicinal Chemistry 2017, 60 (19) , 8131-8144. https://doi.org/10.1021/acs.jmedchem.7b00916
    5. Raphaël Robiette, Tran Trieu-Van, Varinder K. Aggarwal, and Jeremy N. Harvey . Activation of the SN2 Reaction by Adjacent π Systems: The Critical Role of Electrostatic Interactions and of Dissociative Character. Journal of the American Chemical Society 2016, 138 (3) , 734-737. https://doi.org/10.1021/jacs.5b11402
    6. Caroline Proulx, Stan Yoo, Michael D. Connolly, and Ronald N. Zuckermann . Accelerated Submonomer Solid-Phase Synthesis of Peptoids Incorporating Multiple Substituted N-Aryl Glycine Monomers. The Journal of Organic Chemistry 2015, 80 (21) , 10490-10497. https://doi.org/10.1021/acs.joc.5b01449
    7. Alexander A. Andia, Matthew R. Miner, and K. A. Woerpel . Copper(I)-Catalyzed Oxidation of Alkenes Using Molecular Oxygen and Hydroxylamines: Synthesis and Reactivity of α-Oxygenated Ketones. Organic Letters 2015, 17 (11) , 2704-2707. https://doi.org/10.1021/acs.orglett.5b01120
    8. Garrett McKay and Fernando L. Rosario-Ortiz . Temperature Dependence of the Photochemical Formation of Hydroxyl Radical from Dissolved Organic Matter. Environmental Science & Technology 2015, 49 (7) , 4147-4154. https://doi.org/10.1021/acs.est.5b00102
    9. Paul R. Rablen, Brett D. McLarney, Brandon J. Karlow, and Jean E. Schneider . How Alkyl Halide Structure Affects E2 and SN2 Reaction Barriers: E2 Reactions Are as Sensitive as SN2 Reactions. The Journal of Organic Chemistry 2014, 79 (3) , 867-879. https://doi.org/10.1021/jo4026644
    10. Pier Alexandre Champagne, Julien Pomarole, Marie-Ève Thérien, Yasmine Benhassine, Samuel Beaulieu, Claude Y. Legault, and Jean-François Paquin . Enabling Nucleophilic Substitution Reactions of Activated Alkyl Fluorides through Hydrogen Bonding. Organic Letters 2013, 15 (9) , 2210-2213. https://doi.org/10.1021/ol400765a
    11. Eddie Yang, Matthew R. Reese, and John M. Humphrey . Synthesis of α,α-Difluoroethyl Aryl and Heteroaryl Ethers. Organic Letters 2012, 14 (15) , 3944-3947. https://doi.org/10.1021/ol301696x
    12. Samuel Nettey, Christopher A. Swift, Renan Joviliano, Diogo O. Noin, and Scott Gronert . The Impact of Substituents on the Transition States of SN2 and E2 Reactions in Aliphatic and Vinylic Systems: Remarkably Facile Vinylic Eliminations. Journal of the American Chemical Society 2012, 134 (22) , 9303-9310. https://doi.org/10.1021/ja301557a
    13. Shuhei Itoh, Nobuyoshi Yoshimura, Makoto Sato, and Hiroshi Yamataka . Computational Study on the Reaction Pathway of α-Bromoacetophenones with Hydroxide Ion: Possible Path Bifurcation in the Addition/Substitution Mechanism. The Journal of Organic Chemistry 2011, 76 (20) , 8294-8299. https://doi.org/10.1021/jo201485y
    14. Kevin L. Jantzi, Susan Wiltrakis, Lauren Wolf, Anna Weber, Josh Cardinal, and Katie Krieter . The Contrasting Alkylations of 4-(Dimethylaminomethyl)pyridine and 4-(Dimethylamino)pyridine: An Organic Chemistry Experiment. Journal of Chemical Education 2011, 88 (3) , 328-330. https://doi.org/10.1021/ed1000312
    15. Holger Helten,, Tanja Schirmeister, and, Bernd Engels. Theoretical Studies about the Influence of Different Ring Substituents on the Nucleophilic Ring Opening of Three-Membered Heterocycles and Possible Implications for the Mechanisms of Cysteine Protease Inhibitors. The Journal of Organic Chemistry 2005, 70 (1) , 233-237. https://doi.org/10.1021/jo048373w
    16. Tahar Ayad,, Vanessa Faugeroux,, Yves Génisson,, Chantal André,, Michel Baltas, and, Liliane Gorrichon. Stereoselective Access to the Versatile 4-Aminohex-5-ene-1,2,3-triol Pattern. The Journal of Organic Chemistry 2004, 69 (25) , 8775-8779. https://doi.org/10.1021/jo048766v
    17. Diane M. Kalendra and, Barry R. Sickles. Diminished Reactivity of Ortho-Substituted Phenacyl Bromides toward Nucleophilic Displacement. The Journal of Organic Chemistry 2003, 68 (4) , 1594-1596. https://doi.org/10.1021/jo011042o
    18. Bohumil Dolensky and, Kenneth L. Kirk. New Building Blocks for Fluorinated Imidazole Derivatives:  Preparation of β-Fluoro- and β,β-Difluorohistamine. The Journal of Organic Chemistry 2001, 66 (13) , 4687-4691. https://doi.org/10.1021/jo0102415
    19. David Amantini,, Francesco Fringuelli,, Ferdinando Pizzo, and, Luigi Vaccaro. Bromolysis and Iodolysis of α,β-Epoxycarboxylic Acids in Water Catalyzed by Indium Halides. The Journal of Organic Chemistry 2001, 66 (13) , 4463-4467. https://doi.org/10.1021/jo0156215
    20. Scott Gronert. Mass Spectrometric Studies of Organic Ion/Molecule Reactions. Chemical Reviews 2001, 101 (2) , 329-360. https://doi.org/10.1021/cr9900836
    21. Roger J. Griffin,, Christine E. Arris,, Christine Bleasdale,, F. Thomas Boyle,, A. Hilary Calvert,, Nicola J. Curtin,, Christine Dalby,, Sreenivas Kanugula,, Nicola K. Lembicz,, David R. Newell,, Anthony E. Pegg, and, Bernard T. Golding. Resistance-Modifying Agents. 8. Inhibition of O6-Alkylguanine-DNA Alkyltransferase by O6-Alkenyl-, O6-Cycloalkenyl-, and O6-(2-Oxoalkyl)guanines and Potentiation of Temozolomide Cytotoxicity in Vitro by O6-(1-Cyclopentenylmethyl)guanine. Journal of Medicinal Chemistry 2000, 43 (22) , 4071-4083. https://doi.org/10.1021/jm000961o
    22. Jeffrey D. Schloss,, Silvana M. Leit, and, Leo A. Paquette. Radical and Anionic Response of N-(Bromomethanesulfonyl)-Substituted α,α‘-Bridged Piperidine Substrates. The Journal of Organic Chemistry 2000, 65 (21) , 7119-7123. https://doi.org/10.1021/jo000873b
    23. Silvana M. Leit and, Leo A. Paquette. Intramolecular Cyclization of Radicals Generated from α-Halomethylsulfonamides. The Journal of Organic Chemistry 1999, 64 (25) , 9225-9229. https://doi.org/10.1021/jo991344e
    24. Luc Neuville,, Antony Bigot,, Marie Elise Tran Huu Dau, and, Jieping Zhu. 4-Nitrophenyltriflate and 4-Nitrophenylnonaflate as New Perfluoroalkanesulfonyl Transfer Agents:  Experimental and Computational Studies. The Journal of Organic Chemistry 1999, 64 (20) , 7638-7642. https://doi.org/10.1021/jo990559l
    25. Linli He,, Meni Wanunu,, Hoe-Sup Byun, and, Robert Bittman. Regioselective and Stereospecific Azidation of 1,2- and 1,3-Diols by Azidotrimethylsilane via a Mitsunobu Reaction. The Journal of Organic Chemistry 1999, 64 (16) , 6049-6055. https://doi.org/10.1021/jo9906375
    26. Steven Howard and, Stephen G. Withers. Bromoketone C-Glycosides, a New Class of β-Glucanase Inactivators. Journal of the American Chemical Society 1998, 120 (40) , 10326-10331. https://doi.org/10.1021/ja981580r
    27. Patrick Mougenot,, Paul Mertens,, Muriel Nguyen,, Roland Touillaux, and, Jacqueline Marchand-Brynaert. α,ω-Difunctional Perfluorinated Spacer Arms for Polymeric Material Derivatization. The Journal of Organic Chemistry 1996, 61 (1) , 408-412. https://doi.org/10.1021/jo951248n
    28. Jasmin T. Lechner, Christian Riedelsheimer, Simon M. J. Endraß, Nina M. Gerold, Jennifer Heidrich, Burkhard Krumm, Jörg Stierstorfer, Thomas M. Klapötke. Synthesis of Bridged Tetrazoles with Promising Properties and Potential Applications by a One‐Step Finkelstein Reaction. Chemistry – A European Journal 2023, 14 https://doi.org/10.1002/chem.202303021
    29. Mojtaba Khorasani, Babak Karimi, Hojatollah Vali. Coupling of CO 2 with epoxides catalyzed by bifunctional periodic mesoporous organosilica with ionic liquid framework. Reaction Chemistry & Engineering 2022, 7 (12) , 2618-2628. https://doi.org/10.1039/D2RE00290F
    30. Domonkos A. Tasi, Gábor Czakó. Unconventional SN2 retention pathways induced by complex formation: High-level dynamics investigation of the NH2− + CH3I polyatomic reaction. The Journal of Chemical Physics 2022, 156 (18) https://doi.org/10.1063/5.0091789
    31. Kyu Terashima, Tomoko Kawasaki-Takasuka, Ichiro Minami, Takashi Yamazaki. Synthesis and synthetic applications of (4-hydroxyphenyl)perfluoroalkylmethanols. Tetrahedron 2022, 104 , 132574. https://doi.org/10.1016/j.tet.2021.132574
    32. Xin Zhang, Choon-Hong Tan. Stereospecific and stereoconvergent nucleophilic substitution reactions at tertiary carbon centers. Chem 2021, 7 (6) , 1451-1486. https://doi.org/10.1016/j.chempr.2020.11.022
    33. Kyu Terashima, Tomoko Kawasaki-Takasuka, Takashi Yamazaki. Construction of fully substituted carbon centers containing a heteroatom and a CF 3 group via in situ generated p -quinone methides. Organic & Biomolecular Chemistry 2021, 19 (6) , 1305-1314. https://doi.org/10.1039/D0OB02469D
    34. Shen‐Yi Guo, Qing‐Hui Guo, Shuo Tong, Mei‐Xiang Wang. Synthesis of Electron‐Deficient Corona[5]arenes and Their Selective Complexation with Dihydrogen Phosphate: Cooperative Effects of Anion–π Interactions. Angewandte Chemie 2020, 132 (21) , 8155-8160. https://doi.org/10.1002/ange.201915839
    35. Shen‐Yi Guo, Qing‐Hui Guo, Shuo Tong, Mei‐Xiang Wang. Synthesis of Electron‐Deficient Corona[5]arenes and Their Selective Complexation with Dihydrogen Phosphate: Cooperative Effects of Anion–π Interactions. Angewandte Chemie International Edition 2020, 59 (21) , 8078-8083. https://doi.org/10.1002/anie.201915839
    36. Grace E. Klinger, Yuting Zhou, Pengchao Hao, Jacob Robbins, Jake M. Aquilina, James E. Jackson, Eric L. Hegg. Biomimetic Reductive Cleavage of Keto Aryl Ether Bonds by Small‐Molecule Thiols. ChemSusChem 2019, 12 (21) , 4775-4779. https://doi.org/10.1002/cssc.201901742
    37. Ranjit De, Minhyuk Jung, Hohjai Lee. Designing Microparticle-Impregnated Polyelectrolyte Composite: The Combination of ATRP, Fast Azidation, and Click Reaction Using a Single-Catalyst, Single-Pot Strategy. International Journal of Molecular Sciences 2019, 20 (22) , 5582. https://doi.org/10.3390/ijms20225582
    38. Julien Malassis, Jean-Baptiste Vendeville, Qui-Hien Nguyen, Marie Boujon, Quentin Gaignard-Gaillard, Mark Light, Bruno Linclau. Synthesis of vicinal dideoxy-difluorinated galactoses. Organic & Biomolecular Chemistry 2019, 17 (21) , 5331-5340. https://doi.org/10.1039/C9OB00707E
    39. Naoya Shindo, Hirokazu Fuchida, Mami Sato, Kosuke Watari, Tomohiro Shibata, Keiko Kuwata, Chizuru Miura, Kei Okamoto, Yuji Hatsuyama, Keisuke Tokunaga, Seiichi Sakamoto, Satoshi Morimoto, Yoshito Abe, Mitsunori Shiroishi, Jose M. M. Caaveiro, Tadashi Ueda, Tomonori Tamura, Naoya Matsunaga, Takaharu Nakao, Satoru Koyanagi, Shigehiro Ohdo, Yasuchika Yamaguchi, Itaru Hamachi, Mayumi Ono, Akio Ojida. Selective and reversible modification of kinase cysteines with chlorofluoroacetamides. Nature Chemical Biology 2019, 15 (3) , 250-258. https://doi.org/10.1038/s41589-018-0204-3
    40. José Mora, Cristian Cervantes, Edgar Marquez. New Insight into the Chloroacetanilide Herbicide Degradation Mechanism through a Nucleophilic Attack of Hydrogen Sulfide. International Journal of Molecular Sciences 2018, 19 (10) , 2864. https://doi.org/10.3390/ijms19102864
    41. Khaled M. Elattar, Ahmed Fekri, Nesma M. Bayoumy, Ahmed A. Fadda. Sulfones in heterocyclic synthesis: advances in the chemistry of phenyl sulfonylacetophenone. Research on Chemical Intermediates 2017, 43 (7) , 4227-4264. https://doi.org/10.1007/s11164-017-2869-8
    42. Qingsu Cheng, Ashwin Aravind, Matthew Buckley, Andrew Gifford, Bahram Parvin. Functionalized Buckyballs for Visualizing Microbial Species in Different States and Environments. Scientific Reports 2015, 5 (1) https://doi.org/10.1038/srep13685
    43. Jiann-Jyh Huang, Shi-Han Lu, Yu Hsuan Chung, Fung Fuh Wong. Vilsmeier–Haack reagent-promoted formyloxylation of α-chloro-N-arylacetamides by formamide. RSC Advances 2015, 5 (45) , 35934-35939. https://doi.org/10.1039/C5RA05779E
    44. Matthew J. Leonard, Peter G. McKay, Anthony R. Lingham. Bromo–nitro substitution on a tertiary α carbon—a previously uncharacterized facet of the Kornblum substitution. RSC Advances 2015, 5 (93) , 76401-76418. https://doi.org/10.1039/C5RA14798K
    45. Kohei Tagawa, Keita Sasagawa, Ken Wakisaka, Shunsuke Monjiyama, Mika Katayama, Hiroshi Yamataka. Experimental Study on the Reaction Pathway of α-Haloacetophenones with NaOMe: Examination of Bifurcation Mechanism. Bulletin of the Chemical Society of Japan 2014, 87 (1) , 119-126. https://doi.org/10.1246/bcsj.20130253
    46. Jeannette T. Bowler, Freeman M. Wong, Scott Gronert, James R. Keeffe, Weiming Wu. Reactivity in the nucleophilic aromatic substitution reactions of pyridinium ions. Org. Biomol. Chem. 2014, 12 (32) , 6175-6180. https://doi.org/10.1039/C4OB00946K
    47. Pier Alexandre Champagne, Alexandre Saint-Martin, Mélina Drouin, Jean-François Paquin. Triol-promoted activation of C–F bonds: Amination of benzylic fluorides under highly concentrated conditions mediated by 1,1,1-tris(hydroxymethyl)propane. Beilstein Journal of Organic Chemistry 2013, 9 , 2451-2456. https://doi.org/10.3762/bjoc.9.283
    48. Jianglin Hu, Qi Zhang, Zhenhong Guan, Yanlong Gu, Wanling Mo, Tao Li, Guangxing Li. Palladium‐Catalyzed Carbonylation of Chloroacetates to Afford Malonates: Controlling the Selectivity of the Product in a Buffer. ChemCatChem 2012, 4 (11) , 1776-1782. https://doi.org/10.1002/cctc.201200245
    49. Andrew R. Buller, Jason W. Labonte, Michael F. Freeman, Nathan T. Wright, Joel F. Schildbach, Craig A. Townsend. Autoproteolytic Activation of ThnT Results in Structural Reorganization Necessary for Substrate Binding and Catalysis. Journal of Molecular Biology 2012, 422 (4) , 508-518. https://doi.org/10.1016/j.jmb.2012.06.012
    50. Mika Katayama, Keita Sasagawa, Hiroshi Yamataka. Experimental study on the reaction pathway of α‐haloacetophenones with nucleophiles: direct substitution or carbonyl addition?. Journal of Physical Organic Chemistry 2012, 25 (8) , 680-685. https://doi.org/10.1002/poc.2901
    51. Albert J. de Graaf, Enrico Mastrobattista, Cornelus F. van Nostrum, Dirk T. S. Rijkers, Wim E. Hennink, Tina Vermonden. ATRP, subsequent azide substitution and ‘click’ chemistry: three reactions using one catalyst in one pot. Chemical Communications 2011, 47 (24) , 6972. https://doi.org/10.1039/c1cc12224j
    52. Jonathan D. Wilden. The Sulfonamide Motif as a Synthetic Tool. Journal of Chemical Research 2010, 34 (10) , 541-548. https://doi.org/10.3184/030823410X12857514635822
    53. Khaled R.A. Abdellatif, Carlos A. Velázquez, Zhangjian Huang, Morshed A. Chowdhury, Edward E. Knaus. Triaryl (Z)-olefins suitable for radiolabeling with carbon-11 or fluorine-18 radionuclides for positron emission tomography imaging of cyclooxygenase-2 expression in pathological disease. Bioorganic & Medicinal Chemistry Letters 2010, 20 (17) , 5245-5250. https://doi.org/10.1016/j.bmcl.2010.06.155
    54. V. V. Komissarov, A. M. Kritzyn. Polymethylene derivatives of nucleic bases bearing ω-functional groups. VIII. ω-Oxo-ω-phenylalkylpyrimidines and -purines. Russian Journal of Bioorganic Chemistry 2010, 36 (4) , 477-487. https://doi.org/10.1134/S1068162010040060
    55. Toshiaki Yoshimura, Hironori Sakae, Masaki Yoshizawa, Kiyoshi Hasegawa, Eiichi Tsukurimichi. Pyrolysis of α- and β-Heteroatoms Substituted Ethyl Phenyl Sulfoxides. Phosphorus, Sulfur, and Silicon and the Related Elements 2010, 185 (5-6) , 1162-1173. https://doi.org/10.1080/10426501003773563
    56. Christopher Wong, Roger J. Griffin, Ian R. Hardcastle, Julian S. Northen, Lan-Zhen Wang, Bernard T. Golding. Synthesis of sulfonamide-based kinase inhibitors from sulfonates by exploiting the abrogated SN2 reactivity of 2,2,2-trifluoroethoxysulfonates. Organic & Biomolecular Chemistry 2010, 8 (10) , 2457. https://doi.org/10.1039/b922717b
    57. Mohammad Saraji, Ali Akbar Hajialiakbari Bidgoli. Single-drop microextraction with in-microvial derivatization for the determination of haloacetic acids in water sample by gas chromatography–mass spectrometry. Journal of Chromatography A 2009, 1216 (7) , 1059-1066. https://doi.org/10.1016/j.chroma.2008.12.064
    58. Attila Fábián, Ferenc Ruff, Ödön Farkas. Mechanism of nucleophilic substitutions at phenacyl bromides with pyridines. A computational study of intermediate and transition state. Journal of Physical Organic Chemistry 2008, 21 (11) , 988-996. https://doi.org/10.1002/poc.1412
    59. Stephen Duffy, Richard F. Langler. The Displacement of RSO2 Groups from Tetrahedral Carbon. Australian Journal of Chemistry 2008, 61 (6) , 466. https://doi.org/10.1071/CH07237
    60. Navath Suryakiran, Thummalapalli Srikanth Reddy, Yenamandra Venkateswarlu. Iodination of β-keto-sulfones using molecular iodine and hydrogen peroxide in aqueous medium: facile synthesis of α-iodomethyl sulfones. Journal of Sulfur Chemistry 2007, 28 (5) , 471-476. https://doi.org/10.1080/17415990701595865
    61. N. Suryakiran, M. Srinivasulu, Y. Venkateswarlu. Halogenation of β-keto-sulfones using KX/H 2 O 2 in aqueous medium: Synthesis of α-halo β-keto-sulfones and α-halomethyl sulfones. Journal of Sulfur Chemistry 2007, 28 (4) , 345-350. https://doi.org/10.1080/17415990701418738
    62. A. S. Morkovnik, L. N. Divaeva, V. A. Anisimova. Mechanism of the reaction of neutral and anionic N-nucleophiles with α-halocarbonyl compounds. Russian Chemical Bulletin 2007, 56 (6) , 1194-1209. https://doi.org/10.1007/s11172-007-0182-1
    63. Pallab Pahari, Bidyut Senapati, Dipakranjan Mal. 4-Fluorocyclohexa-2,5-dienones as new acceptors for the Hauser annulation. Tetrahedron Letters 2007, 48 (14) , 2635-2638. https://doi.org/10.1016/j.tetlet.2007.01.159
    64. N. Suryakiran, P. Prabhakar, T. Srikanth Reddy, K. Chinni Mahesh, K. Rajesh, Y. Venkateswarlu. Chemoselective mono halogenation of β-keto-sulfones using potassium halide and hydrogen peroxide; synthesis of halomethyl sulfones and dihalomethyl sulfones. Tetrahedron Letters 2007, 48 (5) , 877-881. https://doi.org/10.1016/j.tetlet.2006.11.129
    65. N. Suryakiran, T. Srikanth Reddy, V. Suresh, M. Lakshman, Y. Venkateswarlu. Synthesis of α-iodo β-ketosulfones and α-iodo methylsulfones using iodine monochloride. Tetrahedron Letters 2006, 47 (26) , 4319-4323. https://doi.org/10.1016/j.tetlet.2006.04.123
    66. . Nucleophilic Substitution Reactions of α-Chloroacetanilides with Pyridines in Dimethyl Sulfoxide. Bulletin of the Korean Chemical Society 2005, 776-780. https://doi.org/10.5012/bkcs.2005.26.5.776
    67. Kazuhiro Ikegai, Wanchai Pluempanupat, Teruaki Mukaiyama. Preparation of tert -Alkyl Aryl Sulfides from tert -Alcohols via Quinone-mediated Oxidation–Reduction Condensation between tert -Alkyl Diphenylphosphinites and 2-Sulfanyl-1,3-benzothiazole. Chemistry Letters 2005, 34 (5) , 638-639. https://doi.org/10.1246/cl.2005.638
    68. Germán Fonseca, Gustavo A. Seoane. Chemoenzymatic synthesis of enantiopure α-substituted cyclohexanones from aromatic compounds. Tetrahedron: Asymmetry 2005, 16 (7) , 1393-1402. https://doi.org/10.1016/j.tetasy.2005.02.012
    69. Emmanuelle Briard, Victor W. Pike. Substitution‐reduction: an alternative process for the [ 18 F] N ‐(2‐fluoroethylation) of anilines. Journal of Labelled Compounds and Radiopharmaceuticals 2004, 47 (4) , 217-232. https://doi.org/10.1002/jlcr.816
    70. William R Barton, Leo A Paquette. Generic synthesis of β-sultams via domino alkylation of bromomethanesulfonamides. Canadian Journal of Chemistry 2004, 82 (2) , 113-119. https://doi.org/10.1139/v03-174
    71. Joseph P. Michael, Charles B. de Koning, Tshepo J. Malefetse, Ibrahim Yillah. Preparation and reductive transformations of vinylogous sulfonamides (β-sulfonyl enamines), and application to the synthesis of indolizidines. Org. Biomol. Chem. 2004, 2 (23) , 3510-3517. https://doi.org/10.1039/B413379J
    72. Christine Goze, Jean‐Claude Chambron, Valérie Heitz, Didier Pomeranc, Xavier J. Salom‐Roig, Jean‐Pierre Sauvage, Angeles Farrán Morales, Francesco Barigelletti. Long‐Lived MLCT Excited States‐Ru II Complexes with a Helical Bis‐Phen Ligand. European Journal of Inorganic Chemistry 2003, 2003 (20) , 3752-3758. https://doi.org/10.1002/ejic.200300161
    73. . Kinetics and Mechanism of the Aminolysis of Phenacyl Bromides in Acetonitrile. A Stepwise Mechanism with Bridged Transition State. Bulletin of the Korean Chemical Society 2003, 993-998. https://doi.org/10.5012/bkcs.2003.24.7.993
    74. Yao-Jun Shi, David L. Hughes, James M. McNamara. Stereospecific synthesis of chiral tertiary alkyl-aryl ethers via Mitsunobu reaction with complete inversion of configuration. Tetrahedron Letters 2003, 44 (18) , 3609-3611. https://doi.org/10.1016/S0040-4039(03)00728-7
    75. Giuliana Righi, Paolo Bovicelli, Anna Sperandio. A mild preparation of α-halo-α,β-enones from cyclic enones. Tetrahedron Letters 1999, 40 (32) , 5889-5892. https://doi.org/10.1016/S0040-4039(99)01213-7
    76. VEERLE COESSENS, KRZYSZTOF MATYJASZEWSKI. END GROUP TRANSFORMATION OF POLYMERS PREPARED BY ATRP, SUBSTITUTION TO AZIDES. Journal of Macromolecular Science, Part A 1999, 36 (5-6) , 667-679. https://doi.org/10.1081/MA-100101556
    77. Takashi Yamazaki, Hideki Umetani, Tomoya Kitazume. CuCN and Trimethylsilyl Chloride‐Catalyzed Regiospecific Grignard Reactions to CF 3 ‐Containing Allylic Derivatives. Israel Journal of Chemistry 1999, 39 (2) , 193-205. https://doi.org/10.1002/ijch.199900025
    78. Stanislaw Boryczka. α,ω‐Bis(4‐substituted‐3‐quinolinylthio)alkanes from reactions of thioquinanthrene with alkoxides. Journal of Heterocyclic Chemistry 1998, 35 (6) , 1461-1466. https://doi.org/10.1002/jhet.5570350641
    79. Jen-Wen Yu, Steve K. Huang. SYNTHESIS OF DIETHYL 3-ARYL-3-OXOPROPYLPHOSPHONATES. Organic Preparations and Procedures International 1997, 29 (2) , 214-218. https://doi.org/10.1080/00304949709355187
    80. Dietrich Prescher, Thomas Thiele, Ralf Ruhmann. Various synthetic approaches to fluoroalkyl p-nitrophenyl ethers. Journal of Fluorine Chemistry 1996, 79 (2) , 145-148. https://doi.org/10.1016/S0022-1139(96)03490-2
    81. Giuliana Righi, Giovanna Rumboldt, Carlo Bonini. A simple route to syn α-Amino-β-Hydroxy esters by C-2 regioselective opening of a, β-Epoxy esters with metal halides. Tetrahedron 1995, 51 (48) , 13401-13408. https://doi.org/10.1016/0040-4020(95)00873-7
    82. Jozef Drabowicz, Piotr Kiełbasinski, Marian Mikołajczyk. Synthesis of Sulphoxides. 1995, 109-254. https://doi.org/10.1002/9780470666357.ch3
    83. Shiou‐Chuan Tsai, Hsin‐Ell Wang, Chi‐Tsuan Huang, Lih‐Ming Yiin, Shiuh‐Tzung Liu. Stereospecific Ligand Substitutions in Manganese(I) Complexes. Chemische Berichte 1995, 128 (2) , 151-155. https://doi.org/10.1002/cber.19951280211
    84. Niall W.A. Geraghty. Functions Incorporating a Halogen and a Chalcogen. 1995, 41-93. https://doi.org/10.1016/B0-08-044705-8/00254-5
    85. . References to Volume 4. 1995, 1085-1229. https://doi.org/10.1016/B0-08-044705-8/09012-9
    86. Stefan Pitsch, Esteban Pombo‐Villar, Albert Eschenmoser. Chemie von α‐Aminonitrilen. 13. Mitteilung. Über die Bildung von 2‐Oxoethyl‐phosphaten (“Glycoladehyd‐phosphaten”) aus rac ‐Oxirancarbonitril und anorganischem Phosphat und über (formale) Konstitutionelle Zusammenhänge zwischen 2‐Oxoethyl‐phosphaten und Oligo (hexo‐ und pentopyranosyl)nucleotid‐Rückgraten. Helvetica Chimica Acta 1994, 77 (8) , 2251-2285. https://doi.org/10.1002/hlca.19940770815
    87. Yu. L. Ignatova, N. M. Karimova, I. N. Rozhkov. Nucleophilic substitution of bromine in vicinal bromotrifluoroalkylamines. Russian Chemical Bulletin 1994, 43 (5) , 900-903. https://doi.org/10.1007/BF00717368
    88. Bruce E. Smart. Characteristics of C-F Systems. 1994, 57-88. https://doi.org/10.1007/978-1-4899-1202-2_3
    89. Juan F Gil, Diego J Ramón, Miguel Yus. Intramolecular 1,6-hydride transfer in acyclic 1,6-diols: A mechanistic study. Tetrahedron 1994, 50 (24) , 7307-7314. https://doi.org/10.1016/S0040-4020(01)85254-6
    90. Giorgio Cevasco, Silvana Penco, Sergio Thea. INTRAMOLECULAR PARTICIPATION OF THE SULFINYL GROUP IN THE HYDROLYSIS OF THE ESTER FUNCTION OF AN α-PHOSPHORYL SULFOXIDE. Phosphorus, Sulfur, and Silicon and the Related Elements 1993, 84 (1-4) , 257-260. https://doi.org/10.1080/10426509308034340
    91. André Leblanc, Laurent Fosset, Gilbert Magnaud, Gérard Delmas, Michel Desgranges, Henri Sentenac-roumanou, Claude Lion, Claude Charvy, Ali Mohri. NOUVEAUX DECONTAMINANTS. DESTRUCTION OXYDATIVE D'UN SILIMI DE L'YPERITE: PHENYL-2 CHLORO-2′ DIETHYLSULFURE PAR LE MONOPERSULFATE DE POTASSIUM. Phosphorus, Sulfur, and Silicon and the Related Elements 1993, 79 (1-4) , 141-145. https://doi.org/10.1080/10426509308034407
    92. Juan F. Gil, Diego J. Ramón, Miguel Yus. New masked δ-lithiocarbonyl compounds: preparation and synthetic applications. Tetrahedron 1993, 49 (22) , 4923-4938. https://doi.org/10.1016/S0040-4020(01)80409-9
    93. Clotilde Pichon, Karen R. Clemens, Alan R. Jacobson, A. Ian Scott. On the mechanism of porphobilinogen deaminase. Design, synthesis, and enzymatic reactions of novel porphobilinogen analogs.. Tetrahedron 1992, 48 (23) , 4687-4712. https://doi.org/10.1016/S0040-4020(01)81567-2
    94. Roger D. Amos, Nicholas C. Handy, Peter G. Jones, Anthony J. Kirby, Jane K. Parker, Jonathan M. Percy, Ming Der Su. Bond length and reactivity: the gauche effect. A combined crystallographic and theoretical investigation of the effects of β-substituents on C–OX bond length. J. Chem. Soc., Perkin Trans. 2 1992, 16 (4) , 549-558. https://doi.org/10.1039/P29920000549
    95. I.N. Rozhkov, N.M. Karimova, Yu.L. Ignatova, Yu.A. Borisov. Influence of α-, β- and γ-cf3-groups upon the kinetics of the Sn2 bromine substitution in alkyl bromides. Role of transition state solvatation. Journal of Fluorine Chemistry 1991, 54 (1-3) , 62. https://doi.org/10.1016/S0022-1139(00)83572-1
    96. Sakae Uemura. Oxidation of Sulfur, Selenium and Tellurium. 1991, 757-787. https://doi.org/10.1016/B978-0-08-052349-1.00212-2
    97. T. Kitazume. Ultrasound-promoted stereocontrolled synthesis of fluorinated molecules. Ultrasonics 1990, 28 (5) , 322-325. https://doi.org/10.1016/0041-624X(90)90039-Q
    98. Y. Shimizugawa, T. Takahashi, M. Ishii, T. Yamamoto. EFFECTIVE AND PREFERENTIAL TRANSFORMATION OF COMPOUNDS HAVING 2-HALOETHYL GROUPS ON POSITIVE SULFUR INTO ETHENYL COMPOUNDS UNDER PTC CONDITIONS. Organic Preparations and Procedures International 1990, 22 (4) , 522-525. https://doi.org/10.1080/00304949009356317
    99. Tomoya Kitazume, Takashi Yamazaki, Keizo Ito. Preparation of Optically Pure p -[(1-Hydroxy-2,2,2-trifluoro)ethyl]benzoic Acid. Synthetic Communications 1990, 20 (10) , 1469-1472. https://doi.org/10.1080/00397919008052863
    100. Francis A. Carey, Richard J. Sundberg. Nucleophilic Substitution. 1990, 257-339. https://doi.org/10.1007/978-1-4613-9795-3_5
    Load all citations

    Pair your accounts.

    Export articles to Mendeley

    Get article recommendations from ACS based on references in your Mendeley library.

    Pair your accounts.

    Export articles to Mendeley

    Get article recommendations from ACS based on references in your Mendeley library.

    You’ve supercharged your research process with ACS and Mendeley!

    STEP 1:
    Click to create an ACS ID

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    MENDELEY PAIRING EXPIRED
    Your Mendeley pairing has expired. Please reconnect