Studies on the Free Radical Carbon-Carbon Bond Formation in the Reaction of α-Phosphoryl Sulfides and Selenides with Alkenes

Article abstract of DOI:10.1016/0040-4020(95)00393-M

α-Mono- and α,α-disubstituted α-phosphoryl radicals 9 were generated from the easy accessible α-phosphoryl sulfides 4, 5 and α-phosphoryl selenides 11, 12 and reacted with the electron rich alkenes 6 under the reductive (n-Bu3SnH/AIBN) conditions to give the functionalized phosphonates 7 in 32+68percent yield.Two fragmentation processes of the phosphonate α-alkoxy alkyl radicals are also described. - Key words: α-phosphoryl sulfides, α-phosphoryl selenides, intermolecular radical reaction, radical fragmentation, phosphonates, tri-n-butyltin hydride, α,α'-azaisobutyronitrile