Organotin compound, reaction with

Iodomethyltrialkyltin compounds, R3SnCH2I (from R3SnCl and ICH2ZnI), provide an entry to other functionally substituted organotin compounds. Reaction with nucleophiles such as R10, R1S, R 2N, or R 3P gives further a-substituted derivatives, and carbon nucleophiles can be used to locate the functional groups at more distant positions on the alkyl chain. Some examples are shown in Scheme 3. 

Together with reactions named after Heck and Suzuki, the Stille reac-tion belongs to a class of modern, palladium-catalyzed carbon-carbon bond forming reactions. The palladium-catalyzed reaction of an organotin compound 2 with a carbon electrophile 1 is called Stille coupling. 

Organotin Hydrides, Reactions with Organic Compounds, 1, 47... 

The Stille reaction has developed as a popular protocol for the formation of C-C bonds due to the air- and moisture-stability as well as functional group compatibility of organotin compounds. Together with the Suzuki-Miyaura coupling it is one of the most powerful methods for the synthesis of molecules containing unsymmetrical biaryl moieties. However, despite its efficiency, this versatile reaction has slowly been displaced by other procedures that avoid the use of highly toxic organostannanes. 

Organotin(IV) compounds reactions with nickel Schiff base complexes, 198 Oxidation surface... 

A synergic action of a mixture of epoxy resins with cadmium stearate has been demonstrated in the reaction of radical decomposition of hydroperoxide. This mixture exhibits activity in the inhibition reaction, exceeding not only that expected from a calculation on the basis of additivity, but also the activity of the most energetic inhibitor of peroxide decomposition - cadmium stearate (Fig. 101) [12]. Synergic action in the stabilization of polyvinyl chloride by mixtures of epoxy compounds with lead silicate, mixtures of the autocondensation products of cyclohexanone with lead silicate, as well as mixtures of the autocondensation products of cyclohexanone with organotin compounds and with calcium stearate, is described in [74, 77, 98]. 

Syntheses of dialkylthallium halides with bulky alkyl groups such as trimethyl-silylmethyl and neopentyl have been described, these compounds are dimeric. (Acyloxy)arylthallium compoimds have been prepared from organotin compounds, reactions (40), (41). ... 

Various organotin reagents react with acyl and aroyl halides under mild conditions without decarbonylation to give carbonyl compounds[390,39l]. Alkyl- or alkenyltin reagents react with acyl and aroyl chlorides to give ketones[548.733,734]. One example is the preparation of the a,/3-dnsaturated 7-keto esters 860 and 861, carried out under a CO atmosphere[735]. The reaction has been applied intramolecularly to the synthesis of the macrocyclic keto... 

The reaction is of practical importance in the vulcanization of siUcone mbbers (see Rubber compounding). Linear hydroxy-terrninated polydimethyl siloxanes are conveniently cross-linked by reaction with methyldiethoxysilane or triethoxysilane [998-30-1]. Catalysts are amines, carboxyflc acid salts of divalent metals such as Zn, Sn, Pb, Fe, Ba, and Ca, and organotin compounds. Hydroxy-terrninated polysiloxanes react with Si—H-containing polysiloxanes to... 

These reactions proceed rapidly and in good yield with primary alkyl and phenyl organotin compounds at ca 200°C. The reactions proceed at lower temperatures if anhydrous aluminum chloride is used as a catalyst. 

---