A New Method for the Generation and Cyclization of Iminyl Radicals via the Hudson Reaction

[formula: see text] A mild new synthetic procedure has been developed for in situ generation and cyclization of iminyl radicals onto pendant alkenes, followed by functionalization of the resulting carbon radical by one of a variety of trapping reagents. The key process in the method involves production of the iminyl radical via treatment of an aldoxime or ketoxime with readily available 2,6-dimethylbenzenesulfinyl chloride at -50 degrees C to room temperature (Hudson reaction).