Dichloromethane is one solvent that is used widely in laboratory. It is so stable that it seldom reacts with other materials. There are only a few reports that involves dichloromehane as a reactant. Previous in our laboratory, we discovered a dichloromethane activation product. To study the details of the methylene insertion prouct, [(SCH2S)PS]2Zn form (Et4N)2 (PS3Zn)2, we used monodentate thiols in different condition as models to understand what condition thiols may react with dichloro methane. We found out thiols can react with dichloromethane under strong base. When there is aromatic ring in a thiol, that thiol will react with dichloromethane easily. Adding zinc salts showed that zinc ion is an inhibitor in thiolate/dichloromethane reactions. We synthesized Tris(3-trimethylsilyl-2-thiophenyl)phosphine [H3SiPS3] and SiPS3Zn complex to study the parallel effect of adding bulky silyl substitaents on PS3 ligand towards reaction with dichloromethane. Most conclusion are similar to that of monodentate thiols. There is one thing that differs from the results of monedentate thiols: the SiPS3Zn complex does react with dichloromethane.