Reaction of (triorganostannyl)cyanamides with carbon disulfide

(Triorganostanny)cyanamides were found to react with carbon disulfide to give dicyandiamide, the corresponding bis(triorganotin) sulfide, and the corresponding N,N′-dicyano-N′-(triorganostannyl)-S-(triorganostannyl)isothiourea. (Trimethylstannyl)cyanamide, (tri-n-butylstannyl)cyanamide, and (tribenzylstannyl)cyanamide were prepared for the first time by the reaction of cyanamide with trimethyltin hydroxide, bis(tri-n-butyltin) oxide, and tribenzyltin hydroxide, respectively. The IR spectrum of (trimethylstannyl)cyanamide in the solid state indicates that the trimethyltin group is planar. Bis(trimethylstannyl)carbodiimide and bis(tri-n-butylstannyl)carbodiimide were prepared by the disproportionation of the corresponding (triorganostannyl)cyanamide.