BIS(METHYLTHIO)(TRIMETHYLSILYL)METHANE

Physical properties

bp 67–70°C/10 mmHg.

Uses

Bis(methylthio)(trimethylsilyl)methane is a reagent used for synthesis of bis(methylthio)ketene acetals from aldehydes and ketones;acyl anion synthon for conjugate additions to enones and enoates;useful for one-carbon homologations.
The bis(methylthio)ketene acetals are useful synthetic intermediates because they are readily converted into S-methyl thioesters (eq 9) or the corresponding carboxylic acids and esters.

Preparation

prepared from lithiobis(methylthio)- methane by silylation with chlorotrimethylsilane (eq 1).Both bis(methylthio)methane and chlorotrimethylsilane are commercially available.