Tomasz Białas

A novel synthesis of diethyl 3-iodoalkyl- and 3-iodoalkenylphosphonates via the iodine atom transfer addition reaction

Abstract Diethyl 3-iodoalkyl 7 and 3-iodoalkenylphosphonates 8 as new potent synthetic and bioactive compounds were obtained in 58–100% yields via the iodine atom transfer addition reaction of diethyl 1-iodoalkylphosphonates 1 to alkenes 3 and alkynes 4 in the presence of α,α′-azoisobutyronitrile (AIBN).

A New View of the Mechanistic Pathways in the Iodine Atom Transfer Addition Reaction Involving 1-Iodoalkylphosphonates and Related Nonphosphorus Systems

The title reaction in the initiation step proceeds via two mechanistic pathways involving attack of the isobutyronitrile radical either on the starting iodide or on the starting alkene or alkyne followed by the reaction of the adduct radical with the iodide.