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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 ]
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.
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 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.
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 overall combined transformation of an aldehyde to an alkyne by this method is named after its developers, American chemists Elias James Corey and Philip L. Fuchs. The Corey–Fuchs reaction By suitable choice of base, it is often possible to stop the reaction at the 1-bromoalkyne, a useful functional group for further transformation.
An example is the ozonolysis of eugenol converting the terminal alkene to an aldehyde: [9] By controlling the reaction/workup conditions, unsymmetrical products can be generated from symmetrical alkenes: [10] Using TsOH; sodium bicarbonate (NaHCO 3); dimethyl sulfide (DMS) gives an aldehyde and a dimethyl acetal