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A new, practical access to amidyl radicals.
Cécile Moutrille1, Samir Z Zard
1Laboratoire de Synthese Organique associe au CNRS, Ecole Polytechnique, 91128 Palaiseau, France. zard@poly.polytechnique
Chemical Communications (Cambridge, England)
|August 13, 2004
Summary
Amidyl radicals are generated from N-allylsulfonimides using xanthate and peroxide initiators. This process involves sulfur dioxide extrusion from N-amidosulfonyl radicals, sometimes trapped by internal olefins.
Area of Science:
- Organic Chemistry
- Radical Chemistry
Background:
- N-allylsulfonimides are versatile precursors in organic synthesis.
- Generation of amidyl radicals is crucial for various chemical transformations.
Purpose of the Study:
- To investigate a novel method for generating amidyl radicals.
- To explore the reactivity and reaction pathways of these radicals.
Main Methods:
- Utilizing xanthate and peroxide initiators for radical generation.
- Employing N-allylsulfonimides as starting materials.
- Analyzing reaction intermediates and products.
Main Results:
- Efficient generation of amidyl radicals from N-allylsulfonimides was achieved.
- The process involves sulfur dioxide extrusion from N-amidosulfonyl radicals.
- Premature capture of radicals by internal olefins was observed in some cases.
Conclusions:
- This study presents a new route for amidyl radical generation.
- Understanding the reaction mechanism, including radical trapping, is key for synthetic applications.