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N-Hydroxy-o-benzenedisulfonimide: A Misunderstood Selective Oxidizing Agent.
Margherita Barbero1, Iacopo Degani, Rita Fochi
1Dipartimento di Chimica Generale ed Organica Applicata dell'Università, C.so M. D'Azeglio 48, I-10125 Torino, Italy.
The Journal of Organic Chemistry
|December 13, 1996
Summary
N-Hydroxy-o-benzenedisulfonimide is a versatile selective oxidizing agent, contrary to prior beliefs. It efficiently oxidizes aldehydes, benzyl alcohols, thiols, and sulfides in various chemical reactions.
Area of Science:
- Organic Chemistry
- Oxidation Reactions
Background:
- N-Hydroxy-o-benzenedisulfonimide was previously considered ineffective for oxidation.
- The accessibility and utility of this reagent were not fully explored.
Purpose of the Study:
- To re-evaluate the oxidizing capabilities of N-Hydroxy-o-benzenedisulfonimide.
- To demonstrate its effectiveness as a selective oxidizing agent across various functional groups.
Main Methods:
- Investigated oxidation reactions using N-Hydroxy-o-benzenedisulfonimide.
- Examined the transformation of aldehydes, benzyl alcohols, thiols, and sulfides.
Main Results:
- N-Hydroxy-o-benzenedisulfonimide proved to be a useful selective oxidizing agent.
- Successfully achieved oxidation of aldehydes to acids, benzyl alcohols to aldehydes, thiols to disulfides, and sulfides to sulfoxides.
- 18 examples demonstrated the reagent's broad applicability.
Conclusions:
- N-Hydroxy-o-benzenedisulfonimide is a valuable and selective reagent for organic oxidations.
- The findings challenge previous assumptions about its reactivity and highlight its practical utility.