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2,3-Dichloro-5,6-Dicyanobenzoquinone (DDQ). A New Preparation

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    2,3-Dichloro-5,6-Dicyanobenzoquinone (DDQ). A New Preparation
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    The Journal of Organic Chemistry

    Cite this: J. Org. Chem. 1965, 30, 9, 3240
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    https://doi.org/10.1021/jo01020a529
    Published September 1, 1965
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    This article is cited by 29 publications.

    1. Weiming Chen, Jin Suo, Yongjian Liu, Yuanchao Xie, Mingjun Wu, Fuqiang Zhu, Yifeng Nian, Haji A. Aisa, Jingshan Shen. Industry-Oriented Route Evaluation and Process Optimization for the Preparation of Brexpiprazole. Organic Process Research & Development 2019, 23 (5) , 852-857. https://doi.org/10.1021/acs.oprd.8b00438
    2. Cadmus Chen, Chuan He. Oxidation by Dehydrogenation. 2024https://doi.org/10.1016/B978-0-323-96025-0.00067-3
    3. Hu Cai, Qinglong Zhang, Cheng Huang. Applications and Mechanisms of Oxidative Dehydrogenation to Unsaturated Compounds. 2024https://doi.org/10.1016/B978-0-323-96025-0.00107-1
    4. Runze Zhang, Long Zhang, Sanzhong Luo. Aerobic Organocatalytic Oxidation. 2024https://doi.org/10.1016/B978-0-323-96025-0.00129-0
    5. Meshari A. Alsharif, Qandeel Alam Raja, Nida Abdul Majeed, Rabab. S. Jassas, Abdulrahman A. Alsimaree, Amina Sadiq, Nafeesa Naeem, Ehsan Ullah Mughal, Reem I. Alsantali, Ziad Moussa, Saleh A. Ahmed. DDQ as a versatile and easily recyclable oxidant: a systematic review. RSC Advances 2021, 11 (47) , 29826-29858. https://doi.org/10.1039/D1RA04575J
    6. Xin Tao, Constantin G. Daniliuc, Robert Knitsch, Michael Ryan Hansen, Hellmut Eckert, Maximilian Lübbesmeyer, Armido Studer, Gerald Kehr, Gerhard Erker. The special role of B(C 6 F 5 ) 3 in the single electron reduction of quinones by radicals. Chemical Science 2018, 9 (41) , 8011-8018. https://doi.org/10.1039/C8SC03005G
    7. Alison E. Wendlandt, Shannon S. Stahl. Chinon‐katalysierte, selektive Oxidation organischer Moleküle. Angewandte Chemie 2015, 127 (49) , 14848-14868. https://doi.org/10.1002/ange.201505017
    8. Alison E. Wendlandt, Shannon S. Stahl. Quinone‐Catalyzed Selective Oxidation of Organic Molecules. Angewandte Chemie International Edition 2015, 54 (49) , 14638-14658. https://doi.org/10.1002/anie.201505017
    9. S.F. Kirsch, M. Wegener. 7.01 Oxidation by Dehydrogenation. 2014, 1-25. https://doi.org/10.1016/B978-0-08-097742-3.00701-1
    10. Feng Zhou, Marc‐Oliver Simon, Chao‐Jun Li. Transition‐Metal‐Free One‐Pot Synthesis of Biaryls from Grignard Reagents and Substituted Cyclohexanones. Chemistry – A European Journal 2013, 19 (22) , 7151-7155. https://doi.org/10.1002/chem.201300491
    11. Tse‐Lok Ho, Mary Fieser, Louis Fieser, Rick Danheiser, William Roush, Janice Smith. 2,3‐Dichloro‐5,6‐Dicyano‐1,4‐Benzoquinone ( DDQ ). 2013, 207-209. https://doi.org/10.1002/9780471264194.fos03620.pub5
    12. Tse‐Lok Ho, Mary Fieser, Louis Fieser, Rick Danheiser, William Roush, Janice Smith. 2,3‐Dichloro‐5,6‐Dicyano‐1,4‐Benzoquinone ( DDQ ). 2013, 207-209. https://doi.org/10.1002/9780471264194.fos03620.pub6
    13. Tse‐Lok Ho, Mary Fieser, Louis Fieser, Rick Danheiser, William Roush, Janice Smith. 2,3‐Dichloro‐5,6‐Dicyano‐1,4‐Benzoquinone ( DDQ ). 2011, 248-249. https://doi.org/10.1002/9780471264194.fos03620.pub4
    14. Tse‐Lok Ho, Mary Fieser, Louis Fieser, Rick Danheiser, William Roush, Janice Smith. 2,3‐Dichloro‐5,6‐dicyano‐1,4‐benzoquinone ( DDQ ). 2010, 000-000. https://doi.org/10.1002/9780471264194.fos03620.pub3
    15. Tse‐Lok Ho, Mary Fieser, Louis Fieser, Rick Danheiser, William Roush, Janice Smith. 2,3‐Dichloro‐5,6‐dicyano‐1,4‐benzoquinone ( DDQ ). 2009, 000-000. https://doi.org/10.1002/9780471264194.fos03620.pub2
    16. Tse‐Lok Ho, Mary Fieser, Louis Fieser, Rick Danheiser, William Roush, Janice Smith. 2,3‐Dichloro‐5,6‐dicyano‐1,4‐benzoquinone ( DDQ ). 2006https://doi.org/10.1002/9780471264194.fos03620
    17. J. W. A. Findlay, A. B. Turner. trans ‐4,4′‐Dimethoxystilbene. 2003, 53-53. https://doi.org/10.1002/0471264180.os049.15
    18. E. Vogel, W. Klug, A. Breuer. 1,6‐Methano[10]Annulene. 2003, 11-11. https://doi.org/10.1002/0471264180.os054.02
    19. M. RAVIKANTH, CATALINA ACHIM, JOHN S. TYHONAS, ECKARD MÜNCK, JONATHAN S. LINDSEY. Investigation of Phthalocyanine Catalysts for the Aerobic Synthesis of meso -Substituted Porphyrins. Journal of Porphyrins and Phthalocyanines 1997, 01 (04) , 385-394. https://doi.org/10.1002/(SICI)1099-1409(199710)1:4<385::AID-JPP42>3.0.CO;2-I
    20. Tadao Shingaki, Hiro Kuma, Yoshihiko Kushi, Toshikazu Nagai. Reaction of 9-Diazofluorene with 2,3-Dichloro-5,6-dicyano- p -benzoquinone: The Structure and the Behaviors of the Resulting Product. Bulletin of the Chemical Society of Japan 1989, 62 (2) , 444-450. https://doi.org/10.1246/bcsj.62.444
    21. Melvin S. Newman, Vinod K. Khanna. OXIDATION OF 2,3DICHLOSO-5,6-DICYANOHYDROQUINONE TO 2,3-DICHLORO-5,6-DICYANOBENZOQUINONE. Organic Preparations and Procedures International 1985, 17 (6) , 422-423. https://doi.org/10.1080/00304948509355531
    22. M. Hiroi, N. Ichikawa. DDQ cathodes for seawater cells. Journal of Applied Electrochemistry 1982, 12 (2) , 147-151. https://doi.org/10.1007/BF00616896
    23. Georg Pawlowski, Michael Hanack. A Convenient Synthesis of Trifluoromethyl Substituted Phthalocyanines. Synthetic Communications 1981, 11 (5) , 351-363. https://doi.org/10.1080/00397918108064299
    24. W. Weschke, H.‐J. Timpe, G. Just. Untersuchungen an EDA‐Komplexen von Benzylarylethern. Journal für Praktische Chemie 1979, 321 (4) , 605-612. https://doi.org/10.1002/prac.19793210413
    25. C. S. Menon, Robert K.‐Y. Zee‐Cheng, C. C. Cheng. Synthesis of dimethoxybenz[g]isoquinolines. Journal of Heterocyclic Chemistry 1977, 14 (5) , 905-908. https://doi.org/10.1002/jhet.5570140536
    26. John W. Scott, David R. Parrish, Fred T. Bizzarro. A RAPID AND MILD PROCESS FOR THE OXIDATION OF 2,3-DICHLORO-5,6-DICYANOBENZOQUINONE (DDQ) FROM 2,3-DICHLORO-5,6-DICYANOHYDROQUINONE (DDHQ). Organic Preparations and Procedures International 1977, 9 (2) , 91-94. https://doi.org/10.1080/00304947709355670
    27. Ki Hwan Kim, Gary L. Grunewald. A RAPID, CONVENIENT, HIGH YIELD PROCEDURE FOR THE REGENERATION OF 2,3-DICHLORO-5,6-DICYANOBENZOQUINONE (DDQ) FROM THE CORRESPONDING HYDROQUINONE (DDHQ). Organic Preparations and Procedures International 1976, 8 (3) , 141-143. https://doi.org/10.1080/00304947609355607
    28. Joyce Y. Corey, Michael Dueber, Maria Malaidza. Synthesis and characterization of 10,11-dihydro-5H-dibenzo[b,f]metallepins of group IV. Journal of Organometallic Chemistry 1972, 36 (1) , 49-60. https://doi.org/10.1016/S0022-328X(00)85121-9
    29. E. Ciganek, W. J. Linn, O. W. Webster. Cyanocarbon and polycyano compounds. 1970, 423-638. https://doi.org/10.1002/9780470771242.ch9
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    The Journal of Organic Chemistry

    Cite this: J. Org. Chem. 1965, 30, 9, 3240
    Click to copy citationCitation copied!
    https://doi.org/10.1021/jo01020a529
    Published September 1, 1965
    Request reuse permissions

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