Reaction of Lithiated Bis methylthio methane with Dimethyl Disulfide and Trimethylchlorosilane

9 Reaction of Lithiated Bis(methylthio)methane with Dimethyl Disulfide and Trimethylchlorosilane 

Reactions of organoalkali compounds with disulfides and trialkylchlorosilane are often extremely fast. The usual procedure involves addition of the reagents to a 

These subsequent reactions can be avoided by applying inversed-order addition, i.e., by adding the organometallic compound to the electrophilic reagent, the latter preferably used in excess. In this way excellent yields are obtained in the reactions of bis(methylthio)methyllithium with dimethyl disulfide and trimethylchlorosilane (compare Ref. [2]). 

Trimethylchlorosilane from a bottle that has been frequently opened, may contain dissolved hydrochloric acid this may destroy part of the organolithium compound. 

Brandsma L, Verkruijsse HD (1987) Preparative Polar Organometallic Chemistry, Vol 1, Springer-Verlag 

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