Dual Nature of (Phenylseleno)cobaloxime in the Reaction with 2-Propynyl Derivatives

Article abstract of DOI:10.1246/bcsj.68.3221

Photolysis or thermolysis of (phenylseleno)cobaloxime gives a pair of radicals: phenylseleno radical and cobaloxime radical, which are considered to be equilibrated with the ion pair by a single electron transfer. the radical addition on the acetylenic moiety takes place when the 2-propynyl derivatives have weak leaving groups (OH, OPh, OAc).On the other hand, the ionic substitution with phenylseleno anion takes place on bromies and tosylates.