The Wolff rearrangement is a reaction in organic chemistry in which an α-diazocarbonyl compound is converted into a ketene by loss of dinitrogen with accompanying 1,2-rearrangement. The Wolff rearrangement yields a ketene as an intermediate product, which can undergo nucleophilic attack with … See more In 1902, Wolff discovered that treating diazoacetophenone with silver (I) oxide and water resulted in formation of phenylacetic acid. Similarly, treatment with silver (I) oxide and ammonia formed phenylacetamide. A … See more Wolff rearrangements can be induced under thermolytic, photolytic, and transition-metal-catalyzed conditions. Thermal conditions … See more The Wolff rearrangement has a few retrons, depending on the reaction out of the ketene intermediate. A carboxylic acid derivative with an α-methylene group is a retron for an Arndt … See more The mechanistic pathway of the Wolff-rearrangement has been the subject of much debate, as there are often competing concerted and stepwise mechanisms. … See more While known since 1902, the Wolff rearrangement did not become synthetically useful until the early 1930s, when efficient methods became available to synthesize α … See more • Diazo • Ketene • Arndt-Eistert reaction • Curtius rearrangement • Schmidt reaction See more WebThe classical Wolff-Kishner reduction of ketones (qv) and aldehydes (qv) involves the intermediate formation of a hydrazone, which is then decomposed at high temperatures under basic conditions to give the methylene group, …
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