Reactions of some dicarbonyl compounds. Part III. Oxidation of some β-diketones with alkaline hydrogen peroxide
Reactions of some dicarbonyl compounds. Part III. Oxidation of some β-diketones with alkaline hydrogen peroxide
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DOI：
10.1039/p19750001347
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发表时间：
1975
期刊：
影响因子：
--
通讯作者：
W. Cocker;D. H. Grayson
中科院分区：
文献类型：
--
作者：
W. Cocker;D. H. Grayson
用碱性过氧化氢氧化β-二酮（R1 CO·CR2 R3·COR 4）得到两种类型的酸，这取决于R2和R3的性质。当这两个都是H时，产物是R1 CO2 H、R4 CO2 H和甲酸，甲酸进一步被氧化。当R2为烷基时，产物为R1 CO2 H、R2 CO2 H、R4 CO2 H和R1 R2 CH·CO2 H和/或R2 R4 CH·CO2 H。当R2和R4都是烷基时，产物是R1 R2 R3 C·CO2 H和R4 CO2 H，以及R2 R3 R4 C·CO2 H和R1 CO2 H，这构成了三取代乙酸的有用来源。这些反应的机理进行了讨论，并描述了两个2-烷基-1，3-二酮的一个额外的氧化副反应。
Oxidation of β-diketones (R1CO·CR2R3·COR4) with alkaline hydrogen peroxide affords two types of acid depending upon the nature of R2 and R3. Where both of these are H, the products are R1CO2H, R4CO2H, and formic acid, which suffers further oxidation. Where R2 is alkyl, the products are R1CO2H, R2CO2H, R4CO2H, and R1R2CH·CO2H and/or R2R4CH·CO2H. Where both R2 and R4 are alkyl, the products are R1R2R3C·CO2H and R4CO2H, and R2R3R4C·CO2H and R1CO2H, and this constitutes a useful source of trisubstituted acetic acids. The mechanisms of these reactions are discussed, and an additional oxidative side-reaction of two 2-alkyl-1,3-diketones is described.