Dimethylzinc-initiated radical reaction of cyclic ethers with arylamines, alkoxyamines, and dialkylhydrazines

Dimethylzinc-initiated radical reaction of THF with arylamines afforded aminoalcohols which were derived from the two molecules of THF and one molecule of an arylamine. The reaction seems to proceed via two-consecutive processes, electrophilic and then nucleophilic reactions of THF-derived species. Alkoxyamines and dialkylhydrazines reacted with electrophilic cyclic ether species to give the corresponding oximes and hydrazones of ω-hydroxyalkanal.