Generation and Mesolytic Dynamics of Organoselenane and Selenosilane Radical Ions:  Development of Mechanistically Interesting and Synthetically Useful Chemistry

PET oxidation of PhSe-SePh and R-CH2-Se-R' generates an electrophilic selenium and carbocationic species, respectively. Similarly, one-electron reductive activations of R-CH2-Se-R' and R3-Si-SePh produces alkyl and alkyl silyl radicals, respectively. The possible structure of the reactive electrophilic selenium species is discussed and the fragmentation of -C-Se]*+ is found to be nucleophilic-assisted. These mechanistically interesting studies have been shown to be useful in initiating various synthetic reactions.