Oxidation of Benzyltrialkylstannanes by Iodosylbenzene Catalyzed by Iron Tetrakis(pentafluorophenyl)porphyrin Chloride. Possible Role of Benzyloxy Radicals

Article abstract of DOI:10.1021/jo00122a032

The oxidations of some benzyltrialkylstannanes by iodosylbenzene induced by tetrakis(pentafluorophenyl)porphyrin chloride (TPFP)FeCl have been investigated.Benzaldehydes and benzyl alcohols are the main reaction products, accompanied by minor amounts of 1,2-diarylethanes and benzyl chlorides.A mechanism seems likely involving the formation of a benzyltrialkylstannane cation radical, which undergoes C-Sn bond cleavage to afford a benzyl radical.The formation of 1,2-diarylethane from this radical is straightforward, whereas it is suggested that benzyl alcohol and benzaldehyde result from the disproportionation of a benzyloxy radical, formed in a oxygen transfer reaction from iodosylbenzene to the benzyl radical.In CH2Cl2, benzyl alcohol can also be the result of hydrogen atom abstraction from the solvent by the benzyloxy radical.