Horner–Wadsworth–Emmons Olefination. Arbuzov Reaction Mechanism, Experimental Procedure, and Set Up.

Описание: I set up a Horner–Wadsworth–Emmons reaction. This reaction allows the stereoselective olefination of aldehydes or ketones using stabilized phosphonate carbanions. Phosphonate carbanions are more nucleophilic than the corresponding phosphorus ylides, allowing them to react with a wide range of aldehydes and ketones under milder conditions. Hindered ketones that are typically nonreactive in Wittig reactions can react in Horner–Wadsworth–Emmons olefinations. The reaction favors the formation of (E)-alkenes. When electron-withdrawing phosphonates are employed, the elimination of the oxaphosphetane intermediates accelerates, boosting the production of (Z)-alkenes. This is known as the Still–Gennari modification. In addition to the type of phosphonate used, the selectivity of the reaction can also be influenced by other factors such as the choice of base and solvent. For more details, check out The Chemists’ Cookbook.

The Chemists' Cookbook: https://nrochemistry.com/the-chemists...


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