Tin-free reductive photochemical carboxymethylation of olefins with α- alkylthioacetates

Article abstract of DOI:10.1016/S0040-4039(97)10095-8

An efficient tin-free reductive photochemical carboxymethylation of olefins with α-alkylthioacetates is developed, which (a) is an experimentally simple technique furnishing substituted derivatives of fatty acids in moderate to good yields, (b) is compatible with polar/protic functional groups and solvents, (c) does not require a special reducing reagent, (d) is fairly insensitive to the presence of dissolved oxygen and, generally, does not require degassing prior to irradiation. The critical feature of the mechanism is the 'reluctance' of short-lived MeS' to group- transfer, resulting in hydrogen abstraction from the media.