Phenylthio trimethylsilane

Anion 2 reacts with primary chloroalkanes to afford 1-phenyl-thio- 1-trimethylsilylalkanes in high yields. Mixed P-S ligands for the copolymerization of olefins and carbon monoxide have been prepared by treating o-(diphenylphosphino)benzyl chloride with anion 2 in THF affording the desired ligand in 80% isolated yield (eq 16).2  

Solubility sol organic solvents incompatible with strong acids and strong oxidizing agents. 

Handling, Storage, and Precautions moisture sensitive use in a fume hood. 

Thioacetalization. In the presence of an acid catalyst (zinc iodide, aluminum chloride, anhyd hydrogen chloride, titanium(rV) chloride), (phenylthio)trimethylsilane reacts with aldehydes and ketones at rt or below to form the corresponding thioacetals (eqs 1 and 2). With o, /3-unsaturated aldehydes 

A list of General Abbreviations appears on the front Eruipapers 

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Lewis acid-mediated addition of (phenylthio)trimethylsilane to acryloyl silane takes place to give l,3-bis(phenylthio)-l-trimethylsilylprop-l-ene (18). This compound may be deprotonated with t-butyl lithium at the /J-position and alkylated to give a range... 

The TMSOTf catalysed reaction of (phenylthio)trimethylsilane with aldehydes to give hemithioacetals has been employed in a stereocontrolled route to polyols, via the 1,3-diol synthon shown (equation 25)103. 

Phenylthio trimethylsilane (trimethyl phenylthio silane) [4551-15-9] M 182.4, b 95-99"/12mm, d 0.97. Purification is as for phenyl trimethyl silylmethyl sulfide. 

Displacement of the anomeric benzoyl group by (phenylthio) trimethylsilane proceeds under milder conditions than displacement of the acetoxy group. Zinc(II) iodide induces generation of an oxonium intermediate at room temperature, whereas TMSOTf promotes the displacement at 0 °C. 2.28 Substitution of the anomeric p-nitrobenzoyl group with (phenylthio)trimethyl-silane occurs in the presence of TMSOTf and gives product within 1 h (eq 12). ... 

Nucleophilic Displacement. PhTMS-BF3 0Et2 system has been shown to be useful in the transformation of allylic alcohols to allylic sulfides (eq IS). Preparation of unsymmetrical diaryl sulfides can be achieved by reaction of arenediazonium tetraflu-oroborates with PhSTMS (eq 19). In some cases, addition of cupric sulfide increases the yield of the diaryl sulfides. The use of (phenylthio)trimethylsilane as a coupling partner in palladium catalyzed reactions with aUyl carbonates (eq 20) and aryl iodide (eq 21) has been explored. ... 

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