Tetrahedron

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

GE Keck, TT Wager, SF McHardy

Index: Keck, Gary E.; Wager, Travis T.; McHardy, Stanton F. Tetrahedron, 1999 , vol. 55, # 40 p. 11755 - 11772

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Citation Number: 98

Abstract

An efficient process for the reductive cleavage of N O bonds using samarium diiodide is detailed for a variety of structural types to define the scope and limitations of the method. The reduction is shown to be compatible with base sensitive substrates such as trifluoroacetamide derivatives, which cannot be reduced satisfactorily using aluminum amalgam or sodium amalgam. Direct quenching of the reduction mixture with acylating ...

~70%

~49%

~96%

~86%

~90%

~44%

~83%

~93%

~67%

~63%

Reductive cleavage of N O bonds in hydroxylamine and hydrox...

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