Trimethyltin chloride

Synthesis

Trimethyltin chloride can be prepared by the redistribution reaction of tetramethyltin with tin tetrachloride. : This redistribution reaction is typically performed with no solvent because high temperatures are required and purification is simplified.

A second route to involves treating the corresponding hydroxide or oxide (in the following reaction, trimethyltin hydroxide ) with a halogenating agent such as hydrogen chloride or thionyl chloride (): :

Uses

Trimethyltin chloride is used as a source of the trimethylstannyl group (). For example, it is a precursor to vinyltrimethylstannane (){{cite journal |doi=10.15227/orgsyn.068.0116|title=Palladium-Catalyzed Coupling of Vinyl Triflates with Organostannanes: 4-tert-Butyl-1-vinylcyclohexene and 1-(4-tert-Butylcyclohexen-1-yl)-2-propen-1-one : :

An example of an organolithium reagent reacting with to form a tin-carbon bond is: :

Organotin compounds derived from are useful in organic synthesis, especially in radical chain reactions. is a precursor to compounds used in PVC stabilization. Reduction of trimethyltin chloride with sodium gives hexamethylditin: :

References

References

1. (1994). "Handbook of Data on Organic Compounds". CRC Press.
2. "Trimethyltin chloride".
3. (1990). "Palladium-catalyzed Coupling of Vinyl Triflates with Organostannanes: 4-''tert''-Butylcyclohexen-1-yl)-2-propen-1-one".
4. Davies, A. G.. (2008). "Comprehensive Organometallic Chemistry". Elsevier.
5. (1998). "Inorganic Syntheses".
6. (1981). "Organometallic Syntheses II". Academic Press.