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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 .
Scheme 12-2. Deoxygenation of an α,β-unsaturated carbonyl compound. The mechanism of NaBH 3 CN reduction of α,β-unsaturated tosylhydrazones has been examined using deuterium-labeling. Alkene formation is initiated by hydride reduction of the iminium ion followed by double bond migration and nitrogen extrusion which occur in a concerted ...
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. This approach is called hydrogenation and requires metal catalysts.
The Bamford–Stevens reaction is a chemical reaction whereby treatment of tosylhydrazones with strong base gives alkenes. [1] [2] [3] It is named for the British chemist William Randall Bamford and the Scottish chemist Thomas Stevens Stevens (1900–2000).
The modified Clemmensen reduction allows for the selective deoxygenation of ketones in molecules that contain stable groups such as cyano, amido, acetoxy, and carboalkoxy. Yamamura et al. effectively reduced cholestane-3-one to cholestane using the modified Clemmensen condition and gave the product in high yield (~76%). [13]
Organic redox reactions: the Birch reduction. Organic reductions or organic oxidations or organic redox reactions are redox reactions that take place with organic compounds.In organic chemistry oxidations and reductions are different from ordinary redox reactions, because many reactions carry the name but do not actually involve electron transfer. [1]
The Barton–McCombie deoxygenation is an organic reaction in which a hydroxy functional group in an organic compound is replaced by a hydrogen to give an alkyl group. [1] [2] It is named after British chemists Sir Derek Harold Richard Barton and Stuart W. McCombie. The Barton-McCombie deoxygenation. This deoxygenation reaction is a radical ...