Chloromethyl (trimethylsilyl)methyl sulfide
Chloromethyl (trimethylsilyl)methyl sulfide is a valuable source of thiocarbonyl ylide, which exhibits rapid reactivity in 1-3 dipolar cycloadditions [3+2] or [3+3], leading to the formation of S-heterocycles. The formation of intermediate occurs in the presence of F- anion from salts(CsF, N+Me4F- for example). The versatility of thiocarbonyl ylide is evident in its reaction with a diverse range of substrates. It demonstrates compatibility with aliphatic aldehydes, aryl isothiocyanates, activated four- and five-membered alkenes. By harnessing the unique reactivity of chloromethyl (trimethylsilyl)methyl sulfide and its resulting thiocarbonyl ylide, chemists can access a wide array of S-heterocycles and engage in diverse synthetic transformations.
Synonyms: Chloromethyl (trimethylsilyl)methylsulfide, chloromethylsulfanylmethyl(trimethyl)silane, (((Chloromethyl)thio)methyl)trimethylsilane