Radical oxidation of amides and related compounds with hypervalent tert- butylperoxyiodanes: Synthesis of imides and tert-butylperoxyamide acetals

Article abstract of DOI:10.1016/S0040-4039(99)01032-1

tert-Butylperoxyiodane undergoes oxidation of the methylene groups α to the nitrogen atom of amides (or carbamates) yielding imides or tert- butylperoxyamide acetals, depending on the reaction conditions. A proposed mechanism involves generation of carbon-centered radicals α to the nitrogen atom.