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Nierenstein reactionThe Nierenstein reaction is an organic reaction describing the conversion of an acid chloride into an haloketone with diazomethane.[1][2] Additional recommended knowledge
Reaction mechanismLike the related Arndt-Eistert reaction, this reactions proceeds through a diazoketone intermediate (5). The loss of nitrogen to gives the desired haloketone (2). The synthesis of benzyl chloromethyl ketone from phenylacetyl chloride [3] in fact requires the addition of HCl gas to the diazoketone intermediate for it to succeed. The unassisted reaction failed. ScopeOne original 1924 Nierenstein reaction:[4] and a reaction starting from benzoyl bromide going haywire with formation of the dioxane dimer:[5] References
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This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Nierenstein_reaction". A list of authors is available in Wikipedia. |