Tetrahedron

Oxidative rearrangement of imines to formamides using sodium perborate

P Nongkunsarn, CA Ramsden

文献索引：Nongkunsarn, Pakawan; Ramsden, Christopher A. Tetrahedron, 1997 , vol. 53, # 10 p. 3805 - 3830

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被引用次数: 59

摘要

Oxidation of C-aryl or alkyl-N-arylaldimines 6 or 20 by sodium perborate tetrahydrate (SPB) in trifluoroacetic acid solution gives rearranged N, N-disubstituted formamides 9 and 21. Yields are variable and solvent dependant with the best yields (50–60%) being obtained for electronically neutral C-aryl substituents or Cs-alkyl substituents. Product formation is rationalised in terms of an intermediate oxaziridine 5 that rearranges via acid catalysed O ...