Organotin derivatives of imidazoles

The sodium salts of imidazoles are so readily hydrolyzed that they are only stable in such media as ethanol or liquid ammonia. Sparingly soluble salts, e.g. silver salts, are stable in aqueous medium, and have been utilized for isolation of imidazoles and in the formation of some 1-substituted derivatives, e.g. 1-trityl, 1-glycosyl (Section 4.07.1.3.8). Mercury salts of imidazole are believed to adopt a linear polymeric structure, and results of studies of thallium and tin derivatives suggest that they, too, are polymeric, at least in the solid state. Stable organotin derivatives of imidazoles are non-explosive and often stable in boiling water. 

C. Pettinari Organotin(iv) derivatives of imidazoles, pyrazoles and related pyrazolyl and imidazolyl ligands 1999MGM661... 

Scheme 87 Synthesis of di- and tri-organotin(IV) complexes derivatives of bis(1-methyl-1H-imidazol-2-ylthio)acetate.

The organotin hydride induced rearrangement of a series of derivatized 1,1-difluorocyclo-propanes 6 resulted in the stereoselective formation of the ( )-3,3-difluoroallylic system Reactions were carried out with (l/7-imidazol-l-yl)thiocarbonyloxy derivatives or iodides, in the presence of catalytic amounts of 2,2 -azobisisobutyronitrile, by refluxing in benzene for four hours. 

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