Functionalized bis(1-methylimidazol-2-yl)methane and 1-(1-methylimidazol-2-yl)methyl-3,5-dimethylpyrazole and their reactions

Bis(1-methylimidazol-2-yl)methane and 1-(1-methylimidazol-2-yl)methyl-3,5-dimethylpyrazole [CH2(min)(pz)] could be deprotonated with n-BuLi at the bridging carbon atom. The corresponding anions were inactive in the reaction with Ph3SnCl but reacted with sulfur, followed by reaction with Ph2SnCl2 to give organotin derivatives Ph2ClSnSCH(min)2 (1) and Ph2ClSnSCH(min)(pz) (4) (min = 1-methylimidazol-2-yl and pz = 3,5-dimethylpyrazol-1-yl, respectively). The structure of 1 determined by X-ray structural analyses indicated that bis(1-methylimidazol-2-yl)methylthiolate acted as a bidentate monoanionic κ2-[N,S] chelating ligand. Reaction of 1 with W(CO)5THF yielded heterobimetallic complex Ph2ClSnSCH(min)2W(CO)5 (2), while similar reaction of 4 with W(CO)5THF resulted in the decomposition of 4 to give pyrazole derivative W(CO)5(pzH). The structure of 2 has been confirmed by X-ray structural analyses, showing that 1 coordinated to the tungsten atom through the free nitrogen atom. Reaction of CH2(min)(pz) with W(CO)5THF yielded bidentate chelating complex CH2(min)(pz)W(CO)4, which when treated with n-BuLi, followed by reaction with Ph3SnCl, gave the final product CH2(minSnPh3)(pz)W(CO)4.