Enolic radical derived from acetic acid: a useful radical alternative to acetate enolate in Michael-type reactions

F Foubelo, F Lloret, M Yus

Index: Foubelo, Francisco; Lloret, Francisco; Yus, Miguel Tetrahedron, 1993 , vol. 49, # 37 p. 8465 - 8470

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Citation Number: 13

Abstract

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.