76200-38-9

Upstream product

• 100-68-5 methyl-phenyl-thioether 
• 17873-08-4 (phenylsulfanylmethyl)trimethylsilane 
• 13307-75-0 (phenylthio)methyllithium 
• 76200-52-7 Trimethyl-(2-methyl-1-phenylsulfanyl-butoxy)-silane 
• 108-98-5 thiophenol 
• 3561-67-9 bis(phenylthio)methane 
• 96-17-3 2-Methylbutyraldehyde 
• 78-76-2 s-butyl bromide 
• 75-77-4 chloro-trimethyl-silane 
• 79158-45-5 2-methyl-1,1-bis(phenylthio)butane 

Downstream Products

• 76200-46-9 (1-Benzenesulfinyl-2-methyl-butyl)-trimethyl-silane 
• 91787-38-1 2-methyl-1-phenylsulphonyl-1-trimethylsilylbutane 

Relevant academic research and scientific papers

Synthesis of Aldehydes from Phenylthiotrimethylsilylmethane

Phenylthiotrimethylsilylmethyl-lithium (4) reacts with alkyl halides to give 1-phenylthio-1-trimethylsilylalkanes (5), which can also be prepared by the addition of alkyl-lithium to 1-phenylthio-1-trimethylsilylethene (8), or from bis(phenylthio)acetals (11).The 1-phenylthio-1-trimethylsilylalkanes (5) can be converted into the corresponding aldehyde (15) by oxidation to the sulphoxide (13), thermal rearrangement, and hydrolysis of the resultant O-silyl thioacetal (14).

A NEW METHOD FOR PREPARING 1-PHENYLTHIO-1-TRIMETHYLSILYLALKANES: THE PREPARATION OF α-SILYLCARBANIONS AND OLEFINS.

1-Phenylthio-1-trimethylsilylalkanes(1) are prepared in high yield from 1,1-bis(phenylthio)acetals(2) by reaction with lithium naphthalenide(3) followed by chlorotrimethylsilane. α-Silylcarbanions are formed from the alkanes(1) and lithium naphthalenide(3).Subsequent reaction with carbonyl compounds gave the olefins(4) via the Peterson reaction.

A NEW METHOD FOR CONVERTING ALKYL HALIDES TO HOMOLOGOUS ALDEHYDES

Phenylthiotrimethylsilylmethyl lithium can be alkylated and the product hydrolysed to the aldehydes by oxidation and rearrangement.