Reactions of trimethylstannyl ions with mono-, di- and trichloro-substituted aromatic substrates by the S(RN)1 mechanism

The reactions of Me3Sn- ion with 2-chloropyridine, p-chlorobenzonitrile, o- , m-dichlorobenzenes, 1,3,5-trichlorobenzene, 2,5-, 2,6-, and 3,5-dichlorop yridines give good yields of substitution products. When p-bis-(trimethylst annyl)benzene is treated with Na metal in liquid ammonia, a dianion is form ed, which upon photostimulated reaction with PhCl, affords the disubstituti on product in 70% yield. We suggest that all these reactions occur by the S (RN)1 mechanism of nucleophilic substitution.