An unexpected Sn–Ph cleavage by mercaptoacetic acid

The reaction of triphenyltin chloride and mercaptoacetic acid under mild reaction conditions in the presence of an amine resulted in the cleavage of a Sn–Ph bond. This cleavage reaction was not observed when triphenyltin hydroxide or other triorganotin chlorides were employed. A possible pathway was proposed for the Sn–Ph cleavage. This is a first report of a mercaptoacetate ligand cleavaging Sn–Ph bonds under mild reaction conditions. It is also the first report of using 3J(119Sn–1H) (–Sn–S–CH2) coupling constants to differentiate sulfur containing organotin compounds.