β‐Trimethylsilylethanesulfonyl Chloride

[106018-85-3] C5H13ClO2SSi (MW 200.79) InChI = 1S/C5H13ClO2SSi/c1-10(2,3)5-4-9(6,7)8/h4-5H2,1-3H3 InChIKey = BLPMCIWDCRGIJV-UHFFFAOYSA-N (protection of primary and secondary amines as their sulfonamides, which are cleaved by fluoride ion1) Alternate Name: SESCl. Physical Data: bp 60 °C/0.1 mmHg; yellow oil. Solubility: sol most common organic solvents. Preparative Method: can be most conveniently synthesized from commercially available Vinyltrimethylsilane 1 (eq 1).1 Radical addition of sodium bisulfite to the vinyl group catalyzed by t-butyl perbenzoate yields the sulfonate salt 2 which can be directly converted to SESCl 3 with Phosphorus(V) Chloride. The chloride 3 can then be purified by distillation. The intermediate sulfonate salt 2 is commercially available. The chloride 3 can also be prepared in 62% yield from the salt 2 using Sulfuryl Chloride and Triphenylphosphine (eq 2).2 A less convenient procedure to synthesize SESCl 3 using β-trimethylsilylethylmagnesium chloride 4 and sulfuryl chloride has also been developed (eq 3).1 (1) (2) (3) Handling, Storage, and Precautions: stable liquid that can be stored at room temperature for weeks. Prone to hydrolysis.