On the mechanism of the deoxygenation of secondary alcohols by the reduction of their methyl xanthates by tin hydrides

A new method for the deoxygenation of secondary alcohols

Barton, D. H. R., & McCombie, S. W. (1975) · Journal of the Chemical Society Perkin Transactions 1 · doi:10.1039/p19750001574 · Cited by 1,656 · see citing works

Modern methods for the radical deoxygenation of alcohols

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Steroids and sex hormones. Part 262. The radical induced stannane reduction of selenoesters and selenocarbonates: A new method for the degradation of carboxylic acids to nor‐alkanes and for desoxygenation of alcohols to alkanes

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Radical-Induced Deoxygenation of Primary Alcohols

Barton, D. H. R., Motherwell, W. B., & Stange, A. F. (1981) · Synthesis · doi:10.1055/s-1981-29587 · Cited by 110 · see citing works

Diaryl telluroxides as new mild oxidising reagents

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New and selective reactions and reagents in carbohydrate chemistry

Barton, D. H. R., & Motherwell, W. B. (1981) · Pure and Applied Chemistry · doi:10.1351/pac198153010015 · Cited by 88 · see citing works

Kinetic applications of electron paramagnetic resonance spectroscopy. 25. Radicals formed by spin trapping with di-tert-butyl thioketone

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On the mechanism of reduction of dithiocarbonates (xanthates) with tributylstannane

Barton, D. H. R., Crich, D., Löbberding, A., & Zard, S. Z. (1985) · Journal of the Chemical Society Chemical Communications · doi:10.1039/c39850000646 · Cited by 42 · see citing works

E.s.r. identification of alkoxythiocarbonyl radicals as possible intermediates in barton deoxygenation of alcohols

Barker, P. J., & Backwith, A. L. J. (1984) · Journal of the Chemical Society Chemical Communications · doi:10.1039/c39840000683 · Cited by 33 · see citing works

Preparation of some organotin compounds containing methylthio, phenylthio, and pentafluoro-phenylthio groups

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The Reaction of Carbon Disulfide with Organotin Oxides and Related Substances

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Electron paramagnetic resonance spectra of some radicals from O-alkyl thioesters and O-alkyl selenoesters

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The Ultraviolet Absorption Spectra of Organic Sulfur Compounds. III. Substituted Phenyl Sulfides

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Radical-initiated reduction of chloroformates to alkanes by tri-n-propylsilane: removal of unwanted hydroxy groups from organic molecules

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The free‐radical reaction of tri‐n‐butyltin hydride with disulfides

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Notes - The Preparation of Bis-(ethyl 3,5-dimethylphenoxyacetate)-4,4'-disulfide

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Experimental Requirements for an Efficient Control of Free‐Radical Polymerizations via the Reversible Addition‐Fragmentation Chain Transfer (RAFT) Process

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On the Trail of Xanthates: Some New Chemistry from an Old Functional Group

Zard, S. Z. (1997) · Angewandte Chemie International Edition in English · doi:10.1002/anie.199706721 · Cited by 444 · see citing works

N-Heterocyclic Carbene Boryl Radicals: A New Class of Boron-Centered Radical

Ueng, S., Solovyev, A. Y., Yuan, X., Geib, S. J., Fensterbank, L., Lacôte, E., Malacrìa, M., Newcomb, M., Walton, J. C., & Curran, D. P. (2009) · Journal of the American Chemical Society · doi:10.1021/ja904103x · Cited by 323 · see citing works

Chemistry of β-(Acyloxy)alkyl and β-(Phosphatoxy)alkyl Radicals and Related Species: Radical and Radical Ionic Migrations and Fragmentations of Carbon−Oxygen Bonds

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Rapid Defunctionalization of Carbonyl Group to Methylene with Polymethylhydrosiloxane−B(C6F5)3

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O -Benzyl Xanthate Esters under Ni/Photoredox Dual Catalysis: Selective Radical Generation and Csp3–Csp2 Cross-Coupling

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Working Supramolecular Machines Trapped in Glass and Mounted on a Film Surface We thank the National Science Foundation and the Sandia National Laboratories for supporting this research.

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The invention of radical reactions

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Polymerization of Ethylene through Reversible Addition–Fragmentation Chain Transfer (RAFT)

Dommanget, C., D’Agosto, F., & Monteil, V. (2014) · Angewandte Chemie International Edition · doi:10.1002/anie.201403491 · Cited by 110 · see citing works

Radical chain reduction of alkyl halides, dialkyl sulphides and O-alkyl S-methyl dithiocarbonates to alkanes by trialkylsilanes

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Facile reduction of dithiocarbonates with n-Bu3SnH-Et3B. Easy access to hydrocarbons from secondary alcohols

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A practical method for the reductive cleavage of the sulfide bond in xanthates

Liard, A., Quiclet‐Sire, B., & Zard, S. Z. (1996) · Tetrahedron Letters · doi:10.1016/0040-4039(96)01253-1 · Cited by 88 · see citing works

Chiral bipyrindine and biquinoline ligands: Their asymmetric synthesis and application to the synthesis of trans-whisky lactone

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Alkyl/Glycosyl Sulfoxides as Radical Precursors and Their Use in the Synthesis of Pyridine Derivatives**

Xie, D., Wang, Y., Zhang, X., Fu, Z., & Niu, D. (2022) · Angewandte Chemie International Edition · doi:10.1002/anie.202204922 · Cited by 82 · see citing works

Chemistry of Porphyrin-Appended Cellulose Strands with a Helical Structure: Spectroscopy, Electrochemistry, and in situ Circular Dichroism Spectroelectrochemistry

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On the mechanism of deoxygenation of secondary alcohols by tin hydride reduction of methyl xanthates and other thiocarbonyl derivatives

Barton, D. H. R., Doo, O. J., & Jászberényi, J. C. (1990) · Tetrahedron Letters · doi:10.1016/s0040-4039(00)94480-0 · Cited by 74 · see citing works

Deoxygenative Functionalization of Hydroxy Groups via Xanthates with Tetraphenyldisilane

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Regioselective Enolization and Alkylation of 4-Oxo-N-(9-phenylfluoren-9-yl)proline: Synthesis of Enantiopure Proline−Valine and Hydroxyproline−Valine Chimeras

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Thiocarbonyl chemistry in polymer science

Bingham, N. M., Abousalman-Rezvani, Z., Collins, K., & Roth, P. J. (2022) · Polymer Chemistry · doi:10.1039/d2py00050d · Cited by 66 · see citing works

The Barton‐McCombie Reaction

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Auf der Spur von Xanthaten ‐ neue Chemie einer alten funktionellen Gruppe

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The invention of radical reactions

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Progress of the Barton-McComble Methodology: From tin hydrides to Silanes

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Acylcobalt salophen reagents. Precursors to acyl radical intermediates for use in carbon-to-carbon bond-forming reactions to alkenes

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Macromolecular Design by Interchange of Xanthates: Background, Design, Scope and Applications

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Iridium-Catalyzed Highly Efficient and Site-Selective Deoxygenation of Alcohols

Yang, S., Tang, W., Yang, Z., & Xu, J. (2018) · ACS Catalysis · doi:10.1021/acscatal.8b02495 · Cited by 56 · see citing works

Deoxygenation of alcohols by the reactions of their xanthate esters with triethylsilane: An alternative to tributyltin hydride in the Barton-McCombie reaction

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A practical access to acyl radicals from acyl hydrazides

Bath, S., Laso, N. M., López-Ruíz, H., Quiclet‐Sire, B., & Zard, S. Z. (2002) · Chemical Communications · doi:10.1039/b210764c · Cited by 53 · see citing works

Safe, facile radical-based reduction and hydrosilylation reactions in a microreactor using tris(trimethylsilyl)silane

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Discovery of the RAFT/MADIX Process: Mechanistic Insights and Polymer Chemistry Implications

Zard, S. Z. (2020) · Macromolecules · doi:10.1021/acs.macromol.0c01441 · Cited by 52 · see citing works

Direct Radical Copolymerizations of Thioamides To Generate Vinyl Polymers with Degradable Thioether Bonds in the Backbones

Watanabe, H., & Kamigaito, M. (2023) · Journal of the American Chemical Society · doi:10.1021/jacs.3c01796 · Cited by 51 · see citing works

Radical O→C Transposition: A Metal-Free Process for Conversion of Phenols into Benzoates and Benzamides

Baroudi, A., Alicea, J., Flack, P., Kirincich, J., & Alabugin, I. V. (2011) · The Journal of Organic Chemistry · doi:10.1021/jo102467j · Cited by 51 · see citing works

Reflections on the mechanism of the Barton-McCombie Deoxygenation and on its consequences†

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Totalsynthese von Colombiasin A

Nicolaou, K. C., Vassilikogiannakis, G. E., Mägerlein, W., & Kranich, R. (2001) · Angewandte Chemie · doi:10.1002/1521-3757(20010702)113:13 · Cited by 48 · see citing works

Total Synthesis of (+)‐Machaeriol D with a Key Regio‐ and Stereoselective SN2′ Reaction

Wang, Q., Huang, Q., Chen, B., Lu, J., Wang, H., She, X., & Pan, X. (2006) · Angewandte Chemie International Edition · doi:10.1002/anie.200600006 · Cited by 46 · see citing works

Aromatic Xanthates and Dithiocarbamates for the Polymerization of Ethylene through Reversible Addition–Fragmentation Chain Transfer (RAFT)

Wolpers, A., Bergerbit, C., Ebeling, B., D’Agosto, F., & Monteil, V. (2019) · Angewandte Chemie International Edition · doi:10.1002/anie.201905629 · Cited by 44 · see citing works

The invention of radical reactions. Part XXXI. Diphenylsilane: a reagent for deoxygenation of alcohols via their thiocarbonyl derivatives, deamination via isonitriles, and dehalogenation of bromo- and iodo- compounds by radical chain chemistry

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A novel radical chain reaction of xanthic anhydrides. Further observations on the intermediacy of alkoxy-thiocarbonyl radicals in the Barton-McCombie reaction

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Xanthates and Related Derivatives as Radical Precursors

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Sulfamate Esters Guide C(3)-Selective Xanthylation of Alkanes

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Enantiospecific Total Synthesis of (−)-4-Thiocyanatoneopupukeanane

Srikrishna, A., & Gharpure, S. J. (2001) · The Journal of Organic Chemistry · doi:10.1021/jo0102765 · Cited by 39 · see citing works

Total Synthesis of (15R)- and (15S)-F2t-Isoprostanes by a Biomimetic Process Using the Cyclization of Acyclic Dihydroxylated Octa-5,7-dienyl Radicals

Durand, T., Guy, A., Vidal, J., & Rossi, J. (2002) · The Journal of Organic Chemistry · doi:10.1021/jo0109624 · Cited by 39 · see citing works

Synthesis of Deoxyglycosides by Desulfurization under UV Light

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Enantiospecific total synthesis of phytoalexins, (+)-solanascone, (+)-dehydrosolanascone, and (+)-anhydro-β-rotunol

Srikrishna, A., & Ramasastry, S. S. V. (2005) · Tetrahedron Letters · doi:10.1016/j.tetlet.2005.08.124 · Cited by 35 · see citing works

Insertion of Degradable Thioester Linkages into Styrene and Methacrylate Polymers: Insights into the Reactivity of Thionolactones

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A New Reaction Manifold for the Barton Radical Intermediates: Synthesis of N-Heterocyclic Furanosides and Pyranosides via the Formation of the C1−C2 Bond

Rhee, J. U., Bliss, B. I., & RajanBabu, T. V. (2003) · Journal of the American Chemical Society · doi:10.1021/ja028617z · Cited by 32 · see citing works

Total synthesis of 12-epi-PGF2α

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Facile Reduction of Dithiocarbonates Derived from Secondary Alcohols with n-Bu3SnH–Et3B and Synthesis of 2-Furanthiones and 2-Furanones by Intramolecular Addition of Alkoxythiocarbonyl Free Radicals to Acetylenic Linkages

Nozaki, K., Oshima, K., & Utimoto, K. (1990) · Bulletin of the Chemical Society of Japan · doi:10.1246/bcsj.63.2578 · Cited by 31 · see citing works

Metal‐Free Transformation of Phenols into Substituted Benzamides: A Highly Selective Radical 1,2‐O→C Transposition in O‐Aryl‐N‐phenylthiocarbamates

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Synthesis of 5,6,11-Trideoxytetrodotoxin

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Bioinspired Synthesis of (−)‐PF‐1018

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Radical 1,2‐O→C Transposition for Conversion of Phenols into Benzoates by O‐Neophyl Rearrangement/Fragmentation Cascade

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Functionalized cyclopentanes via radical cyclizations using thiocarbonate derivatives as initiators and terminators

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A Convenient, High Yielding Cleavage of the Thiocarbonyl Group in Xanthates

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A synthesis of the abietane diterpenoid quinone (±)-royleanone via maleoylcobalt technology.

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Polymerization of Ethylene through Reversible Addition–Fragmentation Chain Transfer (RAFT)

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Degradable Diblock Copolymer Vesicles via Radical Ring-Opening Polymerization-Induced Self-Assembly in Aqueous Media

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A general route to 5,6-seco-hexahydrodibenzopyrans and analogues: first total synthesis of (+)-Machaeridiol B and (+)-Machaeriol B

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Treasures from the Free Radical Renaissance Period – Miscellaneous hexenyl radical kinetic data

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Xanthic anhydrides: A novel and convenient source of alkoxythiocarbonyl and alkyl radicals.

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SYNTHESES OF AVENACIOLIDE AND RELATEDbisLACTONES. A REVIEW

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Ruthenium‐Catalyzed O‐ to S‐Alkyl Migration: A Pseudoreversible Barton–McCombie Pathway

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Ring closure of the 6-methylenecyclodecyl radical

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Ethers as hydrogen sources in BF 3 ·OEt 2 promoted reduction of diphenylmethyl alcohols, ethers and esters to hydrocarbons

Li, J., Liu, Q., Shen, H., Huang, R., Zhang, X., Xiong, Y., & Chen, C. (2015) · RSC Advances · doi:10.1039/c5ra14775a · Cited by 20 · see citing works

Synthesis of (+)-makassaric acid, a protein kinase MK2 inhibitor

Basabe, P., Martín, M., Bodero, O., Blanco, A., Marcos, I. S., David Diez, A., & Urones, J. G. (2010) · Tetrahedron · doi:10.1016/j.tet.2010.06.023 · Cited by 20 · see citing works

Enantiospecific synthesis of (−)-2-hydroxy-exo-brevicomin

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Red-Light-Mediated Barton–McCombie Reaction

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Universal Group 14 Free Radical Photoinitiators for Vinylidene Fluoride, Styrene, Methyl Methacrylate, Vinyl Acetate, and Butadiene

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Oxygen–carbon β-bond effects in radical reactions

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High yield reduction of 2-O-trifluoromethanesulphonate esters of α-hydroxylactones to the corresponding 2-deoxylactones by lithium iodide trihydrate

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Aromatic Xanthates and Dithiocarbamates for the Polymerization of Ethylene through Reversible Addition–Fragmentation Chain Transfer (RAFT)

Wolpers, A., Bergerbit, C., Ebeling, B., D’Agosto, F., & Monteil, V. (2019) · Angewandte Chemie · doi:10.1002/ange.201905629 · Cited by 16 · see citing works

One-step selective deoxygenation of alcohols from acyloins

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On the use of S-(4-alkenyl)-dithiocarbonates as mechanistic probes in the barton-McCombie radical deoxygenation reaction

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Novel skeletal rearrangement of hydroindan derivatives into hydroazulenones via an alkoxy radical

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The invention of radical reactions. Part XXXV. A novel radical fission reaction of N-sulfonylthioxocarbamates

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Total synthesis of (±)-β-chamigrene and (±)-laurencenone C via Ireland ester Claisen rearrangement and an intramolecular type II carbonyl ene reaction sequence

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Stereocontrolled Total Synthesis of Polygalolide A

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Regioselective sulfamoylation at low temperature enables concise syntheses of putative small molecule inhibitors of sulfatases

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