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Conversion of N-aromatic amides to O-aromatic esters
Daniel T Glatzhofer1, Raymond R Roy, Kimberly N Cossey
1Department of Chemistry and Biochemistry, The University of Oklahoma, Norman, Oklahoma 73019, USA. dtglatzhofer@chemdept.chem.ou.edu
Organic Letters
|July 6, 2002
Summary
A novel chemical reaction transforms aromatic amides into aromatic esters using N-nitrosamide intermediates. This method allows for efficient synthesis of phenols and offers pathways for polymerization or deamination.
Area of Science:
- Organic Chemistry
- Reaction Mechanisms
Background:
- N-Aromatic secondary amides are versatile organic compounds.
- Efficient synthesis of aromatic esters and phenols is crucial in organic chemistry.
Purpose of the Study:
- To develop a high-yield transformation of N-aromatic secondary amides into O-aromatic esters.
- To explore the utility of N-nitrosamide intermediates in organic synthesis.
- To investigate modifications of the reaction for polymerization and deamination.
Main Methods:
- In situ generation of N-nitrosamide intermediates from aromatic amines or nitro compounds.
- Reaction of N-nitrosamides to form O-aromatic esters.
- Modification of the reaction conditions with methyl methacrylate or toluene.
Main Results:
- High yields of O-aromatic esters were achieved from N-aromatic secondary amides.
- Phenols were readily synthesized from the resulting esters.
- Addition of methyl methacrylate led to polymerization, while toluene addition resulted in deamination.
Conclusions:
- The N-nitrosamide-mediated rearrangement provides an efficient route to O-aromatic esters.
- The reaction mechanism likely involves radical intermediates.
- The reaction offers tunable outcomes, including polymerization and deamination.