 Previously, we have reported that 2-tert-butyliodobenzene (0.1 eq)/Oxone (4 eq) induces Hofmann rearrangement. However, the scope of the reaction was rather narrow; only 2-substituted, electron-rich benzamide gave good yields.  Significant improvements have been made and the scope of the reaction has been widened.  With 10% mol. of 2-tert-butyliodobenzene and 2 equivalents of Oxone, up to 90% of substituted cyclohexa-2,5-diene-1,4-diones were isolated from 12 substituted benzamides. 2-tert-butyliodobenzene is much more efficient as a pre-catalyst than other ortho-substituted iodobenzenes.

Catalytic Hofmann rearrangement/oxidation of carboxamides induced by 2-tert-butyliodobenzene/oxone

245th National Meeting (2013)

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