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The Wolff–Kishner reduction is a reaction used in organic chemistry to convert carbonyl functionalities into methylene groups. [1] [2] In the context of complex molecule synthesis, it is most frequently employed to remove a carbonyl group after it has served its synthetic purpose of activating an intermediate in a preceding step.
The Mozingo reduction, also known as Mozingo reaction or thioketal reduction, is a chemical reaction capable of fully reducing a ketone or aldehyde to the corresponding alkane via a dithioacetal. [ 1 ] [ 2 ] The reaction scheme is as follows: [ 3 ]
Aldehydes and ketones can be reduced respectively to primary and secondary alcohols. In deoxygenation, the alcohol group can be further reduced and removed altogether by replacement with H. Two broad strategies exist for carbonyl reduction. One method, which is favored in industry, uses hydrogen as the reductant.
The mechanism of reductions of aldehydes and ketones by samarium(II) iodide is based primarily on mechanisms elucidated for similar one-electron reducing agents. [12] Upon single-electron transfer, a ketyl dimer iv forms. In the absence of protic solvent, this dimer collapses to form 1,2-diols.
The second step is the deoxygenation of the pinacolate, which yields the alkene, this second step exploits the oxophilicity of titanium. A proposed mechanism when TiCl 4 and Zn(Cu) are used for the coupling of benzophenone, as proposed in a reference. [3] Note that the mechanism may vary when different conditions are used.
The imine is then reduced to an amine by sodium cyanoborohydride. This reaction works on both aldehydes and ketones. The carbonyl can be treated with ammonia, a primary amine, or a secondary amine to produce, respectively, 1°, 2°, and 3° amines. [5] Aromatic ketones and aldehydes can be reductively deoxygenated using sodium cyanoborohydride. [6]
Deoxygenation is a chemical reaction involving the removal of oxygen atoms from a molecule. The term also refers to the removal of molecular oxygen (O 2 ) from gases and solvents, a step in air-free technique and gas purifiers .
The oxidation of primary alcohols to carboxylic acids normally proceeds via the corresponding aldehyde, which is transformed via an aldehyde hydrate (gem-diol, R-CH(OH) 2) by reaction with water. Thus, the oxidation of a primary alcohol at the aldehyde level without further oxidation to the carboxylic acid is possible by performing the reaction ...