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Carbonyl reduction : ウィキペディア英語版 | Carbonyl reduction Carbonyl reduction in organic chemistry is the organic reduction of any carbonyl group containing compound by a reducing agent. Typical carbonyl compounds are ketones, aldehydes, carboxylic acids and esters. A carbonyl group can be reduced to the alcohol or the oxygen atom can be removed altogether, a process called deoxygenation. Many reducing agents are metal hydrides based on boron and aluminum. A second important method is catalytic hydrogenation.〔''Advanced organic chemistry: Structure and mechanisms'' Francis A. Carey, Richard J. Sundberg 2nd Ed.〕Carbonyl reductions are important to the pharmaceutical Industry. ==Mechanism== The reaction mechanism for metal hydride reduction is based on nucleophilic addition of hydride to the carbonyl carbon. In some cases, the alkali metal cation, especially Li+, participates by coordination to the carbonyl oxygen, thereby enhancing the electrophilicity of the carbonyl. Thus, LiAlH4 is more reactive than NaAlH4 because the smaller lithium cation is a better Lewis acid. A crown ether lowers its reactivity. Alkoxide substitution in metal hydrides increases solubility and selectivity. An example is Red-Al. Replacement of H- by electrongative
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