In our research of precursors of tin radicals able to initiate radical chain reactions under mild conditions, a series of triphenyltin derivatives Ph3SnY (Y = H, I, Cl, OTf, OCHO, SnPh3, SPh) is investigated by cyclic voltammetry. The results show that the tin radical Ph3Sn. is only produced from two compounds: by a one-electron oxidation of Ph3SnH or by a one-electron reduction of Ph3-SnI. Therefore electrooxidation of Ph3SnH generates Ph3Sn. which is able to initiate cyclization of haloalkynes. Reduction or oxidation of the other derivatives affords respectively the anion Ph3Sn- or the cation Ph3Sn+ because they are generated at potentials where the radical Ph3Sn. is either reduced or oxidized.
ASJC Scopus subject areas
- Organic Chemistry