Chloromethyl (trimethylsilyl)methyl sulfide

CAS 105850-89-3, Cat. No EN300-253475
Thiocarbonyl ylide precursor

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[1], [2], [3]. 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[1]. It demonstrates compatibility with aliphatic aldehydes, aryl isothiocyanates, activated four- and five-membered alkenes[1], [3]. 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

Selected publication

  1. Synthesis of 4-Polyfluoroalkyl-1,3-Dithiolanes via [3+2] Cycloaddition of Thiocarbonyl Ylide to Polyfluoroalkanethioamides.

    Mykhaylychenko S. S.; Markitanov Y. N.; Rudenko T. V.; Rusanov E. B.; Shermolovich Y. G. Chem Heterocycl Compd 2019, 55 (2), 189–192. DOI: 10.1007/s10593-019-02438-0

  2. Chloromethyl Trimethylsilylmethyl Sulphide as a Parent Thiocarbonyl Ylide Synthon. A Simple Synthesis of Dihydro- and Tetrahydro-Thiophenes.

    Hosomi A.; Matsuyama Y.; Sakurai H. J Chem Soc Chem Commun 1986, 14, 1073. DOI: 10.1039/c39860001073

  3. Construction of Multifunctional Modules for Drug Discovery: Synthesis of Novel Thia/Oxa-Azaspiro[3.4]Octanes.

    Li D. B.; Rogers-Evans M.; Carreira E. M. Org Lett 2013, 15 (18), 4766–4769. DOI: 10.1021/ol402127b