AMIDE-BASED PROTECTING/RADICAL TRANSLOCATING (PRT) GROUPS - GENERATION OF RADICALS ADJACENT TO CARBONYLS BY 1,5-HYDROGEN TRANSFER-REACTIONS OF O-IODOANILIDES

The o-iodoanilide group is shown to be broadly useful for the generation and subsequent reactions of radicals adjacent to carboxyl groups. The results indicate that this group is one of the best ''protecting/radical translocating'' (PRT) groups introduced to date. Beyond its good performance in radical translocation reactions, it is easy to introduce, serves as a reasonable protecting group both before and after the translocation, and (with appropriate modifications) is easy to remove.