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Raphaël Robiette

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Institute of Condensed Matter and Nanosciences

The Robiette Research Group

Research in Organic and Physical Organic Chemistry

Publications


This page lists our publications. Please contact me if you would like to be sent reprints of these articles.

orcidhttps://orcid.org/000-0002-3449-565X

Show graphical abstracts

      2024

      1. Chiral Isochalcogenourea-Catalysed Enantioselective (4+2) Cycloadditions of Allenoates
        Vogl, L. S.; Mayer, P.; Robiette, R.;* Waser, M.*
        Angew. Chem. Int. Ed. 2024, 63, e202315345.

        2. 2023

      2. One-Carbon Homologation of a,b-Unsaturated Aldehydes: Access to a-Tertiary b,g-Unsaturated Aldehydes
        Delbrassinne, A.; Takam Mba, B.J.; Collard, L.; Robiette, R*
        Eur. J. Org. Chem. 2023, e202300765.

      3. Thiol S- Conjugate Profiles: A Comparative Investigation on Dual Hop and Grape Must with Focus on Sulfanylalkyl Aldehydes and Acetates Adducts
        Chenot, C.; Robiette, R; Haest, S; Collin, S.*
        J. Am. Soc. Brew. Chem. 2022, 81, 23-32

        4. 2022

      4. First evidence of the glutathione S-conjugate of 3-sulfanylheptanol in green malt: discrepancy with the ubiquitous 5- and 6-C analogues
        Chenot, C.; Robiette, R; Collin, S.*
        J. Inst. Brew. 2022, 128, 43-51.

        5. 2021

      5. Cycloaddition of cyclopropanes for the elaboration of medium-sized carbocycles
        Caillé, J.;* Robiette, R.*
        Org. Biomol. Chem. 2021, 19, 5702-5724.

      6. Divergent Rearrangements of Vinylcyclopropane into Skipped Diene and Cyclopentene: Mechanism, Scope and Limitations
        Delbrassinne, A.; Richald, M.; Janssens, J.; Robiette, R.*
        Eur. J. Org. Chem. 2021, 2862-2868.

      7. Sterically Hindered Ortho-Substituted Phosphatriptycenes as Configurationally Stable P-Chirogenic Triarylphosphines
        Hu, L.; Mahaut, D.; Tumanov, N.; Wouters, J.; Collard, L.; Robiette, R.;* Berionni, G.*
        Dalton Trans. 2021, 50, 4772-47777.

      8. A Modular, Low Footprint and Scalable Flow Platform for the Expedient a-Aminohydroxylation of Enolizable Ketones
        Horst Kassin, V.-E.; Morodo, R.; Toupy, T.; Jacquemin, I.; Van Hecke, K.; Robiette, R.; Monbaliu, J.-C. M.*
        Green Chem. 2021, 23, 2336-2351.

        9. 2020

      9. Beta-lactams to act on the endocannabinoid system
        Morelle, A.; Caruano, J.; Feledziak, M.; Michaux, C.; Perpete, E. A.; Muccioli, G. G.; Marchand-Brynaert, J.; Robiette, R.*
        Chimie Nouvelle 2020, 134, 41-49

        10. 2019

      10. Synthesis and characterization of a 5-membered ring cyclic hydroxylamine coupled to triphenylphosphonium to detect mitochondrial superoxide by EPR spectrometry
        Scheinok, S.; Driesschaert, B.; d'Hose, D.; Sonveaux, P.; Robiette, R.; Gallez, B.*
        Free Rad. Res., 2019, 1135-1143.

      11. Complementary Synthetic Approaches toward 9-Phosphatriptycene and Structure–Reactivity Investigations of Its Association with Sterically Hindered Lewis Acids
        Hu, L.; Mahaut, D.; Tumanov, N.; Wouters, J.; Robiette, R.;* Berionni, G.*
        J. Org. Chem., 2019, 84, 11268-11274.

      12. Unexpected Vinylcyclopropane Rearrangement: New Strategies Toward Skipped Dienes using Sulfonium Ylides
        Richald, M.; Delbrassinne, A.; Robiette, R.*
        Eur. J. Org. Chem., 2019, 3779-3782.

      13. First Evidence of the Cysteine and Glutathione Conjugates of 2 3?Sulfanylpentan-1-ol in Hop (Humulus lupulus L.)
        Chenot, C.; Robiette, R.; Collin, S.*
        J. Agr. Food. Chem., 2019, 67, 4002-4010.

        14. 2018

      14. Highly (Z)?Diastereoselective Synthesis of Trifluoromethylated exo-Glycals via Photoredox and Copper Catalysis
        Frédéric, C. J.-M.; Cornil, J.; Vandamme, M.; Dumitrescu, L.; Tikad, A.; Robiette, R.; Vincent, S.*
        Org. Lett. 2018, 20, 6769-6773

      15. Synthesis of Cyclic Organic Carbonates Using Atmospheric Pressure CO2 and Charge-Containing Thiourea Catalysts
        Fan, Y.; Tiffner, M.; Schörgenhumer, J.; Robiette, R.; Waser, M.;* Kass S. R.*
        J. Org. Chem. 2018, 83, 9991-10000

      16. Asymmetric Sulfur Ylide Mediated Formal (4+1) Annulation Reaction: Scope and Mechanism
        Clergue, S.; Rousseau, O.; Delaunay, T.; Dequirrez, G.; Tran, T.V.; El Aakchioui, S.; Barozzino-Consiglio, G.; Robiette, R.*
        Chem. Eur. J. 2018, 11417-11425
        Selected as Hot paper

      17. Syntheses of Highly-Functionalized Spirocyclohexenes by Formal (4+2)-Annulation of Arylidene Azlactones with Allenoates
        Eitzinger, A.; Zielke, K.; Widhalm, M.; Robiette, R.;* Waser, M.*
        Asian J. Org. Chem. 2018, 7, 1620-1625.

      18. Effective Antimalarial Activities of a-Hydroxy Diynes Isolated from Ongokea gore
        Ntumba, J. K.;* Tshiongo, C. M.; Mifundu, M. N.; Robiette, R.; Taba, K. M.*
        Planta Med. 2018, 84, 806-812.

        19. 2017

      19. Investigation of 2-Sulfanylethyl Acetate Cysteine-S-Conjugate as a Potential Precursor of Free Thiols in Beer
        Kankolongo Cibaka, M.-L.; Hang Tran, T. T.; Gros, J.; Robiette, R.; Collin, S.*
        J. Am. Soc. Brew. Chem. 2017, 3, 228-235.

      20. On the Origin of the E/Z Selectivity in the Synthesis of Tetrasubstituted Olefins by Wittig Reaction of a-FluoroPhosphonium Ylides: An Explanation for the Low Stereoselectivity Observed in Reactions of a-Alkoxy Aldehydes
        Depré, D.;* Vermeulen, W. A. A.; Lang, Y.; Dubois, J.; Vendevivere, J.; Vandermeersch, J.; Huang, L.; Robiette, R.*
        Org. Lett. 2017, 19, 1414-1417.

      21. Physico-chemical properties of diacetylenic light fuel oil from Congolese oleaginous plant Ongokea gore (Hua) Pierre
        Ntumba, J. K.;* Mulula, A.; Kashishi, K. T.; Mifundu, M. M.; Robiette, R.; Taba, K. M.
        J. Appl. Chem. 2017, ID 7176317.

      22. Asymmetric synthesis of 2,3-dihydrobenzofurans via a (4+1) annulation between ammonium ylides and in situ generated ortho-quinone methides
        Meisinger, N.; Roiser, L.; Monkowius, U.; Himmelsbach, M.; Robiette, R.;* Waser, M.*
        Chem. Eur. J. 2017, 23, 5137-5142.

      23. On the Origin of the Stereoselectivity in Chiral Amide-Based Ammonium Ylide-Mediated Epoxidations
        Novacek, J.; Robiette, R.; Waser, M.*
        Monatshefte für Chemie 2017, 148, 77-81.

        24. 2016

      24. 3-Sulfanyl-4-methylpentan-1-ol in Dry-Hopped Beers: First Evidence of Glutathione S-Conjugates in Hop (Humulus lupulus L.)
        Kankolongo Cibaka, M.-L.; Decourrière, L.; Lorenzo-Alonso, C.-J.; Bodart, E.; Robiette, R.; Collin, S.*
        J. Agric. Food Chem. 2016, 64, 8572-8582.

      25. Biologically Active b-Lactams: Synthesis and Natural Sources
        Caruano, J.; Muccioli, G. G.; Robiette, R.*
        Org. Biomol. Chem. 2016, 10134-10156.

      26. Towards a General Understanding of Carbonyl-Stabilised Ammonium Ylide-Mediated Epoxidation Reactions
        Novacek, J.; Roiser, L.; Zielke, K.; Robiette, R.;* Waser, M.*
        Chem. Eur. J. 2016, 22, 11422-11428.

      27. Benzylic Ammonium Ylide-Mediated Epoxidations
        Roiser, L.; Robiette, R.;* Waser, M.*
        Synlett 2016, 27, 1963-1968.

      28. Activation of the SN2 Reaction by Adjacent pi Systems: The Critical Role of Electrostatic Interactions and of Dissociative Character
        Robiette, R.;* Trieu-Van, T.; Aggarwal, V. K.,* Harvey, J. N.*
        J. Am. Chem. Soc. 2016, 138, 734-737.
        Among the most read articles of the month in Jan 2016.

        29. 2015

      29. Formal Asymmetric (4+1) Annulation Reaction between Sulfur Ylides and 1,3-Dienes
        Rousseau, O.; Delaunay, T.; Dequirez, G.; Trieu-Van, T.; Robeyns, K.; Robiette, R.*
        Chem. Eur. J. 2015, 21, 12899-12902.

      30. Isolation of a Series of Fatty Acid Components of Ongokea Gore Seed (Isano) Oil and Their Detailed Structural Analysis
        Ntumba J. K.; Collard, L.; Taba, K. M.; Robiette, R.*
        Lipids 2015, 50, 313-322.

      31. Asymmetric Syntheses of Three-Membered Heterocycles Using Chiral Amide-Based Ammonium Ylides
        Pichler, M.; Novacek, J.; Robiette, R.; Poscher, V.; Himmelsbach, M.; Monkowius, U.; Mûller, N.; Waser, M.*
        Org. Biomol. Chem. 2015, 13, 2092-2099.

        32. 2014

      32. Ongokea Gore (isanic) oil: analysis of its chemical composition and its valorisation by derivatisation
        Ntumba, J. K.; Taba, K. M.; Robiette, R.*
        Chimie Nouvelle 2014, 117, 12-20.

      33. Synthesis of Monosubstituted 1,1-Dicarbonyl Ester 1,3-Dienes
        Rousseau, O.; Delaunay, T.; Robiette, R.*
        Synlett 2014, 519.

      34. Formation of four-membered heterocycles
        Robiette, R.;* Marchand-Brynaert, J.
        In Comprehensive Organic Synthesis, 2nd ed.; Molander, G.; Knochel, P. (Eds.); Elsevier, Vol. 5, 2014, 85-128.

      35. (S)-1-(Pent-4’-enoyl)-4-(hydroxymethyl)-azetidin-2-one derivatives as inhibitors of human fatty acid amide hydrolase (hFAAH): synthesis, biological evaluation and molecular modelling
        Caruano, J.; Feledziak, M.; Labar, G.; Michaux, C.; Perpète, E. A.; Muccioli, G. G.; Robiette, R.; Marchand-Brynaert, J.*
        J. Enz. Inhib. Med. Chem. 2014, 29, 654-662.

        36. 2013

      36. Development of a regioselective N-methylation of (benz)imidazoles providing the more sterically hindered isomer
        Van Den Berge, E.; Robiette, R.*
        J. Org. Chem. 2013, 78, 12220-12223. 

      37. New 5-aryl-1H-imidazoles display in vitro antitumor activity against apoptosis-resistant cancer models, including melanomas, through mitochondrial targeting
        Mathieu,V.;* Van Den Berge, E.; Ceusters, J.; Konopka, T.; Cops, A.; Bruyère, C.; Pirker, C.; Berger, W.; Trieu-Van, T.; Serteyn, D.; Kiss, R.; Robiette, R.*
        J. Med. Chem. 2013, 56, 6626-6637.

      38. Comprendre les réactions pour mieux les développer et les utiliser
        Robiette, R.;* Caruano, J.; Rousseau, O.; Tran, T.-V.; Van Den Berge, E.
        Chimie Nouvelle 2013, 113, 18-20.

      39. On the Origin of E/Z Selectivity in the Modified Julia Olefination: Importance of the Elimination Step
        Robiette, R.;* Pospíšil, J.*
        Eur. J. Org. Chem. 2013, 836-840.

      40. First evidence of the production of odorant polyfunctional thiols by bottle refermentation
        Nizet, S.; Gros, J.; Peeters, F.; Chaumont, S.; Robiette, R.; Collin, S.*
        J. Am. Soc. Brew. Chem. 2013, 15-22.

      41. Polycyclic phosphonic acid derivatives obtained by a [4+2] cycloaddition strategy using phosphonodienes
        Villemin, E.; Robeyns, K.; Robiette, R.; Herent, M.-F.; Marchand-Brynaert, J.*
        Tetrahedron 2013, 69, 1138-1147.

        42. 2012

      42. Configurationally stable tetrathiarylmethyl molecular propeller
        Driesschaert, B.; Robiette, R.; Le Duff, C. S.; Collard, L.; Robeyns, K.; Gallez, B.; Marchand-Brynaert, J.*
        Eur. J. Org. Chem. 2012, 6517-6525.
        It was featured on the cover.

      43. Julia-Kocienski reaction-based 1,3-diene synthesis: Aldehyde-dependent (E,E/E,Z)-selectivity
        Billard, F.; Robiette, R.; Pospíšil, J.*
        J. Org. Chem. 2012, 77, 6358-6364.
        Highlighted on Organic Chemistry Portal.

      44. Laser control in open quantum systems: Preliminary analysis towards the Cope rearrangement control in methyl-cyclopentadienylcarboxylate dimer
        Dive, G.; Robiette, R.; Chenel, A.; Ndong, M.; Meier, C.; Desouter-Lecomte, M*
        Theor. Chem. Acc. 2012, 131, 1236.

      45. Practical synthesis of b-oxo benzo[d]-thiazolyl sulfones: Scope and limitations
        Pospíšil, J.;* Robiette, R.; Sato, H.; Debrus, K.
        Org. Biomol. Chem. 2012, 10, 1225-1234.

        46. 2011

      46. Planar Chirality of Imidazole-Containing Macrocycles - Understanding and Tuning Atropisomerism
        Van Den Berge, E.; Pospíšil, J.; Tran, T.-V.; Collard, L.; Robiette R.*
        Eur. J. Org. Chem. 2011, 6649-6655.

      47. Novel phosphonated bicyclic frameworks from Diels-Alder reaction as chelating agents of di- and trivalent metal cations
        Villemin, E.; Elias, B.; Robiette R.; Robeyns, K.; Herent, M.-F.; Habib-Jiwan, J.-L.; Marchand-Brynaert, J.*
        Tetrahedron Lett. 2011, 52, 5140-5144.

      48. Chiral Properties of Tetrathiatriarylmethyl Spin Probes
        Driesschaert, B.; Robiette R.; Lucaccioni, F.; Gallez B.; Marchand-Brynaert, J.*
        Chem. Comm. 2011, 47, 4793-4795.

        49. 2010

      49. A practical synthesis of 1,2-nitroamines by Michael addition of N-nucleophiles to nitroalkenes
        Robiette R.;* Tran, T.-V.; Cordi, A.; Tinant, B.; Marchand-Brynaert, J.*
        Synthesis 2010, 3138-3142.

      50. Synthesis and Biological Evaluation of Novel Imidazole-Containing Macrocycles
        Nshimyumukiza, P.; Van Den Berge, E.; Delest, B.; Mijatovic, T.; Kiss, R.; Marchand-Brynaert, J.; Robiette R.*
        Tetrahedron 2010, 66, 4515-4520.

      51. Engineering Solid-State Molecular Switches N-salicylidene N-Heterocycle Derivatives
        Robert, F.; Naik, A.D.; Hidara, F.; Tinant, B.; Robiette, R.; Wouters, J.; Garcia Y.*
        Eur. J. Org. Chem. 2010, 621-637.
        It was featured on the cover.

        52. 2009

      52. Insights into the Origin of Solid-State Photochromism and Thermochromism of N-salicylideneanils: The Intriguing Case of Aminopyridines
        Robert, F.; Naik, A. D.; Tinant, B.; Robiette, R.; Garcia Y.*
        Chem. Eur. J. 2009, 15, 4327-4342

      53. (R)-4-phenyloxazolidin-2-thione: an efficient chiral auxiliary for [4+2] cycloaddition of 1-aminodiene and activated phosphonodienophiles
        Monbaliu, J.-C.; Robiette, R.; Peeters, D.; Marchand-Brynaert, J.*
        Tetrahedron Lett. 2009, 50, 1314-1317

        54. 2008

      54. Divergent and regioselective synthesis of 2,3,4- and 2,3,5-trisubstituted imidazoles
        Delest, B.; Nshimyumukiza, P.; Fasbender, O.; Marchand-Brynaert, J.; Tinant, B.; Darro, F.;* Robiette, R.*
        J. Org. Chem. 2008, 73, 6816-6823.

      55. Reactions of Silyl-Stabilized Sulfur Ylides with Organoboranes: Enantioselectivity, Mechanism, and Understanding
        Howells, D.; Robiette, R.; Fang, G. Y.; Knowles, L. S.; Woodrow, M. D.; Harvey, J. N.;* Aggarwal, V. K.*
        Org. Biomol. Chem. 2008, 6, 1185-1189.
        It was featured on the cover.

      56. Diastereoselective synthesis of vinylcyclopropanes from dienes and sulfur ylides
        Robiette, R.;* Marchand-Brynaert, J.
        Synlett 2008, 517-520.
        Highlighted on Organic Chemistry Portal

        57. 2007

      57. Mechanism of the Morita-Baylis-Hillman Reaction: A Computational Investigation
        Robiette, R.; Aggarwal, V. K.;* Harvey, J. N.*
        J. Am. Chem. Soc. 2007, 129, 15513-15525.
        Among the most accessed articles in Oct-Dec 2007.

      58. A Stereoselective Approach to 1,3-Aminoalcohols Protected as Cyclic Carbamates: Kinetic versus Thermodynamic Control
        Broustal, G.; Ariza, X.; Campagne, J.-M.;* Garcia, J.;* Georges, Y.; Marinetti, A.; Robiette, R.*
        Eur. J. Org. Chem. 2007, 4293-4297.
        Highlighted in Chem. Eur. J.

        59. 2006

      59. QM and QM/MM Studies of Selectivity in Organic and Bioorganic Chemistry
        Harvey, J. N.;* Aggarwal, V. K.; Bathelt, C. M.; Carreón-Macedo, J.-L.; Gallagher, T. C.; Holzmann, N.; Mulholland A. J.; Robiette R.
        J. Phys. Org. Chem., 2006, 19, 608 - 615.

      60. Mechanism and Diastereoselectivity of Aziridine Formation from Sulfur Ylides and Imines: A Computational Study
        Robiette, R.*
        J. Org. Chem., 2006, 71, 2726 - 2734.

      61. Reactivity and Selectivity in the Wittig Reaction: A Computational Study
        Robiette, R.; Richardson, J.; Aggarwal, V. K.*; Harvey, J. N.*
        J. Am. Chem. Soc., 2006, 128, 2394 - 2409.

      62. Delineation of the factors governing reactivity and selectivity in epoxide formation from ammonium ylides and aldehydes
        Robiette, R.; Conza, M.; Aggarwal, V. K.*
        Org. Biomol. Chem., 2006, 4, 621 - 623.

      63. Highly Enantioselective Synthesis of Glycidic Amides Using Camphor-Derived Sulfonium Salts. Mechanism and Applications in Synthesis
        Aggarwal, V. K.;* Fuentes, D.; Harvey, J. N.; Hynd. G.; Ohara, D.; Picoul, W.; Robiette, R.; Smith, C.; Vasse, J.-L.; Winn. C. L.
        J. Am. Chem. Soc., 2006, 128, 2105 - 2114.

      64. Is phenyl a good migrating group in the rearrangement of organoborates generated from sulfur ylides?
        Robiette, R.; Fang.G. Y.; Harvey, J. N.;* Aggarwal, V. K.*
        Chem. Comm., 2006, 741 - 743.

        65. 2005

      65. On the Origin of High E Selectivity in the Wittig Reaction of Stabilized Ylides: Importance of Dipole-Dipole Interactions
        Robiette, R.; Richardson, J.; Aggarwal, V. K.*; Harvey, J. N.*
        J. Am. Chem. Soc., 2005, 127, 13468 - 13469.

      66. On the Importance of Leaving Group Ability in Reaction of Ammonium, Oxonium, Phosphonium and Sulfonium Ylides
        Aggarwal, V. K.;* Harvey, J. N.;* Robiette, R.
        Angew. Chem., Int. Ed., 2005, 44, 5468 - 5471.
        Highlighted as Hot Paper in Angewandte

      67. Theoretical approach of steric effects in the Diels-Alder Reaction
        Boulanger, M.-L.; Leyssens, T.; Robiette, R.; Peeters D.*
        J. Mol. Struct. (THEOCHEM), 2005, 731, 101 - 106.

      68. A novel strategy towards aminophosphonic derivatives based on the Diels-Alder cycloaddition: experimental and theoretical approaches
        Robiette, R.; Defacqz, N.; Peeters, D.; Marchand-Brynaert, J.*
        Current Org. Synth., 2005, 2, 453 - 477.

        69. 2004

      69. Stereochemistry and conformation of amido-phosphono-cyclohexene derivatives, assigned by NMR and X-Ray diffraction analyses
        Tinant, B.*; Defacqz, N.; Robiette, R.; Touillaux, R.; Marchand-Brynaert, J.
        Phosphorus, Sulfur and Silicon and the Related Elements, 2004, 179, 389 - 402.

        70. 2003

      70. Crystal structure of (S)-3-(Z-1',3'-butadienyl)-4-phenylthiazoline-2-one, C13H13NOS, a chiral 1-amino-diene useful in Diels-Alder cycloaddition reactions
        Tinant, B.*; Robiette, R.; Marchand-Brynaert, J.
        Z. Kristallogr. NCS, 2003, 218, 475 - 476.

      71. Design of a New and Highly Effective Chiral Auxiliary for Diels-Alder Reaction of 1-Aminodiene
        Robiette, R.; Cheboub-Benchaba, K.; Peeters, D.; Marchand-Brynaert, J.*
        J. Org. Chem., 2003, 68, 9809 - 9812.

      72. Analysis of electronic reorganisation in reaction molecules
        Peeters, D.; Leyssens, T.; Robiette, R.
        Chimie Nouvelle, 2003, 82, 91 - 95

      73. [4+2] Cycloaddition of 1-Amidodienes and 2-Substituted Vinylphosphonates: Application to Asymmetric Synthesis of 3-Amino-5-phosphono-1-cyclohexene Derivatives
        Robiette, R.; Defacqz, N.; Stofferis, J.; Marchand-Brynaert, J.*
        Tetrahedron, 2003, 59, 4167 - 4175.

      74. A Study of the rearrangement products of chiral alkylated 1,3-oxazolidine- and thiazolidine-2-thiones
        Robiette, R.; Dekoker-Malengreau, A.; Marchand-Brynaert, J.*
        Heterocycles, 2003, 60, 523 - 536.

        75. 2002

      75. Influence of Diene Subtitution on Transition State Stabilization in Diels-Alder Reactions
        Robiette, R.; Marchand-Brynaert, J.; Peeters, D.*
        J. Org. Chem., 2002, 67, 6823 - 6826.

      76. Theoretical Study of the Influence of Phosphonate Substituents on Diels-Alder Reactions
        Robiette, R.; Marchand-Brynaert, J.; Peeters, D.*
        J. Mol. Struct. (Theochem), 2002, 587, 159 - 169.

        77. 2001

      77. Asymmetric synthesis of b- and g-amidophosphonates by Diels-Alder reaction using chiral amidodiene: theoretical and experimental study of the facial selectivity of chiral N-dienyl lactam
        Robiette, R.; Marchand-Brynaert, J.*
        J. Chem. Soc., Perkin Trans 2, 2001, 11, 2155 - 2158.

      78. [4+2] Cycloaddition of phosphoryl-substituted dienes and dienophiles with a view of preparing aminophosphonic acid derivatives
        Marchand-Brynaert, J.; Defacqz, N.; Robiette, R.
        In Recent Res. Develop. In Org. Chem., 2001, Vol 5, 207 - 223.


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