How does diazomethane react with a diketone?

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SUMMARY

The reaction of 1-phenylbuta-1,3-dione with diazomethane in the presence of ether results in the formation of a diazoketone intermediate. The positively charged nitrogen of diazomethane attacks one of the carbonyl carbons, leading to the formation of a nitrogen-oxygen bond. This reaction is not classified under the Nierenstein reaction but is related to the Büchner–Curtius–Schlotterbeck reaction. Understanding this mechanism is crucial for predicting the products of similar reactions involving diketones and diazomethane.

PREREQUISITES
  • Understanding of carbonyl chemistry
  • Familiarity with diazomethane and its reactivity
  • Knowledge of ether solvents and their role in organic reactions
  • Basic grasp of named reactions in organic chemistry
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  • Study the Büchner–Curtius–Schlotterbeck reaction in detail
  • Learn about the mechanisms of carbonyl compound reactions with nucleophiles
  • Research the properties and applications of diazomethane in organic synthesis
  • Explore the role of ether as a solvent in organic reactions
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Chemistry students, organic chemists, and researchers interested in reaction mechanisms involving diketones and diazomethane.

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Homework Statement


What are the products when 1-phenylbuta-1,3-dione reacts with diazomethane in
presence of ether?


Homework Equations





The Attempt at a Solution


I tried to do it this way:
Since carbonyl carbons of 1-phenylbuta-1,3-dione , one of them might get attacked by the positively charged nitrogen of diazomethane ;and the oxygen ,will therefore (maybe?), bond with the other nitrogen . And then I think the ether will do something but the problem is I can't reason out what happens next or is this approach even correct or not.:confused::cry:
Is this some named reaction ? I tried to google it and stumbled upon the Nierenstein reaction but that is not exactly this reaction , right?:confused:
Any hint or help will be REALLY appreciated.
Thanks in advance.:biggrin:
 
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