Dakin反应
Dakin反应是指芳香醛酮在碱性条件下通过过氧化氢氧化得到酚的反应。反应中先形成芳基甲酸或链状烷烃酸中间体进而皂化得到酚。邻位和对位的+M取代基 (NH2, OH)对反应有利。
反应机理：
同 Baeyer-Villiger 氧化
最新文献：
Oxidation of aromatic aldehydes and ketones by H2O2/CH3ReO3 in ionic liquids: a catalytic efficient reaction to achieve dihydric phenols
R. Bernini, A. Coratti, G. Provenzano, G. Fabrizi, D. Tofani, Tetrahedron, 2005, 61, 1821-1825.
The Urea-Hydrogen Peroxide Complex: Solid-State Oxidative Protocols for Hydroxylated Aldehydes and Ketones (Dakin Reaction), Nitriles, Sulfides, and Nitrogen Heterocycles
R. S. Varma, K. P. Naicker, Org. Lett., 1999, 1, 189-191.
Aerobic Organocatalytic Oxidation of Aryl Aldehydes: Flavin Catalyst Turnover by Hantzsch's Ester
S. Chen, F. W. Foss, Jr, Org. Lett., 2012, 14, 5150-5153.
Organocatalytic Dakin Oxidation by Nucleophilic Flavin Catalysts
S. Chen, M. S. Hoassain, F. W. Foss, Jr, Org. Lett., 2012, 14, 2806-2809.
编译自：Organic Chemistry Portal
相关介绍
碱性条件下芳基醛酮通过过氧化氢氧化得到酚的反应。反应机理同Baeyer–Villiger氧化类似。邻位和对位的给电子取代基 (NH2, OH)对反应有利。
反应机理
反应实例
无溶剂的Dakin氧化反应
参考文献
1. Dakin, H. D. Am. Chem. J. 1909, 42, 477-498. Henry D. Dakin (1880-1952) was born in London, England. During WWI, he invented his hypochlorite solution (Dakin’s solution), which became a popular antiseptic for the treatment of wounds. After the Great War, he emmigrated to New York, where he investigated the B vitamins.
2. Hocking, M. B.; Bhandari, K.; Shell, B.; Smyth, T. A. J. Org. Chem. 1982, 47,
4208-4215.
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5. Guzmán, J. A.; Mendoza, V.; García, E.; Garibay, C. F.; Olivares, L. Z.; Maldonado, L. A. Synth. Commun. 1995, 25, 2121-2133.
6. Jung, M. E.; Lazarova, T. I. J. Org. Chem. 1997, 62, 1553-1555.
7. Varma, R. S.; Naicker, K. P. Org. Lett. 1999, 1, 189-191.
8. Lawrence, N. J.; Rennison, D.; Woo, M.; McGown, A. T.; Hadfield, J. A. Bioorg.
Med. Chem. Lett. 2001, 11, 51-54.
9. Teixeira da Silva, E.; Camara, C. A.; Antunes, O. A. C.; Barreiro, E. J.; Fraga, C. A.M. Synth. Commun. 2008, 38, 784-788.
10. Alamgir, M.; Mitchell, P. S. R.; Bowyer, P. K.; Kumar, N.; Black, D. St. C. Tetrahedron 2008, 64, 7136-7142.
11. Chen, S.; Foss, F. W. Org. Lett. 2012, 14, 5150-5153.
Henry D. Dakin (1880-1952)生于英国伦敦。第一次世界大战期间，他发明了次氯酸溶液（Dakin 溶液），广泛用于伤口的杀菌。战后移民到纽约，在那里他进行了对维生素B的研究。
编译自：Name Reactions （A Collection of Detailed Reaction Mechanisms）, Jie Jack Li, Dakin oxidation，page 190-191.