Aryliminodimagnesium Reagents. XI. Two-Electron Oxidation of the Reagent Molecules in the Reaction with Some Oxidizing Agents and with Strongly Push-Pull Substituted α-Benzylideneacetophenones

Article abstract of DOI:10.1246/bcsj.60.1741

The reactions of an aryliminomagnesium reagent (ArN(MgBr)2) with four oxidizing agents ((i): I2, OsO4, C6H5IO2, I2O5) and four push-pull substituted α-benzylideneacetophenones (ii) were examined.In the reactions with (i), the maximum yield of sym-azobenzene was 50percent.In the reactions with (ii), in addition to products formed via condensation and the typical radical processes, unexpected products formed via cleavages of C=C and C_β-H bonds were observed.Summarizing these results, a pathway involving the formation of arylnitrene-like species via disproportionation of arylaminyl radicals has been proposed.