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McFadyen-Stevens reactionThe McFadyen-Stevens reaction is a chemical reaction best described as a base-catalyzed thermal decomposition of acylsulfonylhydrazides to aldehydes. Additional recommended knowledgeDudman has developed an alternative hydrazide reagent. Reaction mechanismThe mechanism of the McFadyen-Stevens reaction is still under investigation. Two groups have independently proposed a heterolytic fragmentation mechanism.nitrogen gas, and an aryl sulfinate ion (5). The mechanism involves the deprotonation of the acyl sulfonamide followed by a 1,2-proton migration to give the alkoxide (3). The collapse of the alkoxide results in the fragmentation producing the desired aldehyde (4),Martin et al. have proposed a different mechanism involving an acyl nitrene. References
See alsoCategories: Organic redox reactions | Rearrangement reactions |
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "McFadyen-Stevens_reaction". A list of authors is available in Wikipedia. |