C-M Bond Cleavage

Thus irradiation of 168 or 169 in the presence of 1,4-naphthalenedicarbonitrile gave 170 and 171 in 84 and 61% yields, respectively [323]. The mechanism for these reactions is analogous to that suggested for the preceding examples but the yields for the a-silylated sulfides proved far inferior to those of the corresponding a-stannyl sulfides. 

As mentioned previously in this review, a-stannylation lowers the oxidation potentials of alkyl aryl and vinyl aryl sulfides. This lowering depends on the overlap between the C-Sn bond and sulfur p-orbital. Substantial lowering of the 

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