Imidyl Radicals. The Chemistries of 1,8-Naphthalenedicarboximidyl and Phthalimidyl Radicals

Article abstract of DOI:10.1021/jo00375a038

The chemistries of 1,8-naphthalenedicarboximidyl (N^.) and phthalimidyl (P^.) radicals are described.Hydrogen abstractions from alkanes and additions to olefins and benzene proceed in high yield.The low cost of phthalimide, coupled with the absence of a parasitic ring-opening reaction for P^., makes N-bromophthalimide an economical reagent for low-selectivity brominations.The chemistry of N^. resembles that of other imidyl radicals (succinimidyl, glutarimidyl) with respect to selectivities.Conversely, P^. is somewhat of a maverick among imidyl radicals, being slightly more selective in its reactions, but still 10²-10³ less selective than Br^..