Reductive cleavage of NO bonds in hydroxylamines and hydroxamic acid derivatives using samarium diiodide

✍ Scribed by Gary E. Keck; Travis T. Wager; Stanton F. McHardy

• Publisher: Elsevier Science
• Year: 1999
• Tongue: French
• Weight: 887 KB
• Volume: 55
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(99)00486-x

✦ Synopsis

An efficient process for the redoctive cleavage of N-O bonds using samarium diiodide is detailed for a variety of slructural types to define the scope and limitations of the method. The reduction is shown to be compatible with base sensitive substrates such as lrifluoroacetamide derivatives, which cannot be reduced satisfactorily using aluminum amalgam or sodium amalgam. Direct quenching of the reduction mixture with acylating agents is demonstrated to provide high yields of protected amines in a one-pot process from the N-O derivatives.