Nierenstein reaction
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The Nierenstein reaction is an organic reaction describing the conversion of an acid chloride into an haloketone with diazomethane.[1][2]
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[edit] Reaction mechanism
Like 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.
[edit] Scope
One original 1924 Nierenstein reaction:[4]
and a reaction starting from benzoyl bromide going haywire with formation of the dioxane dimer:[5]
[edit] References
- ^ Clibbens, D.; Nierenstein, M. (1915). "The action of diazomethane on some aromatic acyl chlorides". J. Chem. Soc. 107: 1491. doi:.
- ^ Bachman, W. E.; Struve, W. S. (1942). "{{{title}}}". Org. React. 1: 38. (Review)
- ^ McPhee, W. D; Klingsberg, E. Organic Syntheses, Coll. Vol. 3, p.119 (1955); Vol. 26, p.13 (1946). (Article)
- ^ M. Nierenstein, D. G. Wang, and J. C. Warr (1924). "The Action of Diazomethane on some Aromatic Acyl Chlorides II. Synthesis of Fisetol". J. Am. Chem. Soc. 46 (11): 2551 - 2555. doi:.
- ^ H. H. Lewis, M. Nierenstein, and Enid M. Rich (1925). "The Action of Diazomethane on some Aromatic Acyl Chlorides III. The Mechanism of the Reaction". J. Am. Chem. Soc. 47 (6): 1728 - 1732. doi:.
