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Mechanism of the oxidation of trialkylboranes

Cite this: J. Org. Chem. 1967, 32, 6, 1713–1717
Publication Date (Print):June 1, 1967
https://doi.org/10.1021/jo01281a004
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This article is cited by 29 publications.

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  2. Desta Doro Bume, Stefan Andrew Harry, Thomas Lectka, Cody Ross Pitts. Catalyzed and Promoted Aliphatic Fluorination. The Journal of Organic Chemistry 2018, 83 (16) , 8803-8814. https://doi.org/10.1021/acs.joc.8b00982
  3. Juan C. Tuberquia, Nabijan Nizamidin, Robert R. Harl, Jake Albert, Jason Hunter, Bridget R. Rogers and G. Kane Jennings. Surface-Initiated Polymerization of Superhydrophobic Polymethylene. Journal of the American Chemical Society 2010, 132 (16) , 5725-5734. https://doi.org/10.1021/ja9086193
  4. William J. Atkins, Jr.,, Elizabeth R. Burkhardt, and, Karl Matos. Safe Handling of Boranes at Scale. Organic Process Research & Development 2006, 10 (6) , 1292-1295. https://doi.org/10.1021/op068011l
  5. Cyril Ollivier and, Philippe Renaud. Organoboranes as a Source of Radicals. Chemical Reviews 2001, 101 (11) , 3415-3434. https://doi.org/10.1021/cr010001p
  6. T. Chinnusamy, K. Feeney, C.G. Watson, D. Leonori, V.K. Aggarwal. 7.22 Oxidation of Carbon–Boron Bonds. 2014, 692-718. https://doi.org/10.1016/B978-0-08-097742-3.00726-6
  7. M. Yu. Zaremski, E. S. Garina, M. E. Gurskii, Yu. N. Bubnov. Organoboranes-atmospheric oxygen systems as unconventional initiators of radical polymerization. Polymer Science Series B 2013, 55 (5-6) , 304-326. https://doi.org/10.1134/S1560090413050072
  8. Seiichiro Fujisawa, Yoshinori Kadoma. Tri-n-Butylborane/WaterComplex-Mediated Copolymerization of Methyl Methacrylate with Proteinaceous Materials and Proteins: A Review. Polymers 2010, 2 (4) , 575-595. https://doi.org/10.3390/polym2040575
  9. Jung-Ho Son, Michael A. Pudenz, James D. Hoefelmeyer. Reactivity of the Bifunctional Ambiphilic Molecule 8-(dimesitylboryl)quinoline: Hydrolysis and Coordination to CuI, AgI and PdII. Dalton Transactions 2010, 39 (45) , 11081. https://doi.org/10.1039/c0dt00798f
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  11. Yuexian Li, Mihaela Plesescu, Patrick Sheehan, J. Scott Daniels, Shimoga R. Prakash. Synthesis of four isotopically labeled forms of a proteasome inhibitor, bortezomib. Journal of Labelled Compounds and Radiopharmaceuticals 2007, 50 (5-6) , 402-406. https://doi.org/10.1002/jlcr.1173
  12. Jason Labutti, Ian Parsons, Ron Huang, Gerald Miwa, Liang-Shang Gan, J. Scott Daniels. Oxidative Deboronation of the Peptide Boronic Acid Proteasome Inhibitor Bortezomib:  Contributions from Reactive Oxygen Species in This Novel Cytochrome P450 Reaction. Chemical Research in Toxicology 2006, 19 (4) , 539-546. https://doi.org/10.1021/tx050313d
  13. Teresa Pekol, J. Scott Daniels, Jason Labutti, Ian Parsons, Darrell Nix, Elizabeth Baronas, Frank Hsieh, Liang-Shang Gan, Gerald Miwa. HUMAN METABOLISM OF THE PROTEASOME INHIBITOR BORTEZOMIB: IDENTIFICATION OF CIRCULATING METABOLITES. Drug Metabolism and Disposition 2005, 33 (6) , 771-777. https://doi.org/10.1124/dmd.104.002956
  14. Christine Cadot, Peter I. Dalko, Janine Cossy, Cyril Ollivier, Rachel Chuard, Philippe Renaud. Free-Radical Hydroxylation Reactions of Alkylboronates. The Journal of Organic Chemistry 2002, 67 (21) , 7193-7202. https://doi.org/10.1021/jo0201833
  15. . References. 2002, 247-256. https://doi.org/10.1016/B978-012174651-3/50014-8
  16. Christine Cadot, Peter I Dalko, Janine Cossy. Hydroxylation of olefins using molecular oxygen via alkylboronic esters. Tetrahedron Letters 2001, 42 (9) , 1661-1663. https://doi.org/10.1016/S0040-4039(00)02337-6
  17. Sara Wu, Wanda Waugh, Valentino J. Stella. Degradation Pathways of a Peptide Boronic Acid Derivative, 2‐Pyz‐(CO)‐Phe‐Leu‐B(OH)2. Journal of Pharmaceutical Sciences 2000, 89 (6) , 758-765. https://doi.org/10.1002/(SICI)1520-6017(200006)89:6<758::AID-JPS7>3.0.CO;2-L
  18. T.C. Chung, W. Janvikul. Borane-containing polyolefins: synthesis and applications. Journal of Organometallic Chemistry 1999, 581 (1-2) , 176-187. https://doi.org/10.1016/S0022-328X(99)00087-X
  19. Ludmila Scoles, Sandro Gambarotta. Preparation and characterization of a new series of Ti(III) hydroborates supported by silazanate ligands. Inorganica Chimica Acta 1995, 235 (1-2) , 375-380. https://doi.org/10.1016/0020-1693(95)90079-L
  20. F. M. Macdonald, V. M. Lingard. B. 1993, 91-202. https://doi.org/10.1007/978-1-4899-7270-5_2
  21. Derek H.R. Barton, Dominique Bridon, Samir Z. Zard. The invention of radical reactions. Part XVIII. Decarboxylative radical addition to arsenic, antimony, and bismuth phenylsulphides - a novel synthesis of nor-alcohols from carboxylic acids. Tetrahedron 1989, 45 (9) , 2615-2626. https://doi.org/10.1016/S0040-4020(01)80092-2
  22. Herbert C. Brown, M.Mark Midland. Organoboranes for synthesis. 6.. Tetrahedron 1987, 43 (18) , 4059-4070. https://doi.org/10.1016/S0040-4020(01)83444-X
  23. Herbert C. Brown, M. Mark Midland, George W. Kabalka. Organoboranes for synthesis. 5. Tetrahedron 1986, 42 (20) , 5523-5530. https://doi.org/10.1016/S0040-4020(01)88155-2
  24. ANDREW PELTER. Rearrangements Involving Boron. 1980, 95-147. https://doi.org/10.1016/B978-0-12-481302-1.50007-4
  25. . Bibliography. 1975, 230-285. https://doi.org/10.1016/B978-0-12-526550-8.50013-7
  26. Donald S. Matteson. Free-Radical and Photochemical Reactions. 1974, 267-312. https://doi.org/10.1016/B978-0-12-481150-8.50012-3
  27. Herbert C. Brown, M. Mark Midland. Organische Synthesen durch Verdrängung freier Radikale aus Organoboranen. Angewandte Chemie 1972, 84 (15) , 702-710. https://doi.org/10.1002/ange.19720841503
  28. Herbert C. Brown, M. Mark Midland. Organic Synthesesvia Free-Radical Displacement Reactions of Organoboranes. Angewandte Chemie International Edition in English 1972, 11 (8) , 692-700. https://doi.org/10.1002/anie.197206921
  29. A. Suzuki, N. Miyaura, M. Itoh. Reaction of organoboranes with α-lithium furan. Tetrahedron 1971, 27 (13) , 2775-2783. https://doi.org/10.1016/S0040-4020(01)98068-8

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