Enolic Radical Derived from Acetic Acid: A Useful Radical Alternative to Acetate Enolate in Michael-Type Reactions

Article abstract of DOI:10.1016/S0040-4020(01)81929-3

The reaction of iodoacetic acid 1 with tributyltin chloride and sodium borohydride in the presence of different electrophilic olefins 2 (methyl, allyl or tert-butyl acrylates, N,N-dimethyl or N,N-di-iso-propyl acrylamides, acrylonitrile, methyl methacrylate, methacrylonitrile and 1,1-dichloroethylene) and AIBN as an initiator yields, after treatment with aqueous sodium fluoride, the corresponding products 3 through a radical Michael-type process.