76200-41-4

Upstream product

• 100-39-0 benzyl bromide 
• 1443045-55-3 4,4,5,5-tetramethyl-2-(phenylthio)-1,3,2-dioxaborolane 
• 1822-73-7 phenylthioethylene 
• 13307-75-0 (phenylthio)methyllithium 
• 3561-67-9 bis(phenylthio)methane 
• 591-51-5 phenyllithium 
• 62762-20-3 1-phenylthio-1-trimethylsilylethene 
• 75-77-4 chloro-trimethyl-silane 
• 931-59-9 benzenesulfenyl chloride 
• 754-05-2 ethenyltrimethylsilane 
• 882-33-7 diphenyldisulfane 
• 17873-08-4 (phenylsulfanylmethyl)trimethylsilane 
• 100-68-5 methyl-phenyl-thioether 

Downstream Products

• 76200-50-5 2-phenyl-1-phenylsulfinyl-1-(trimethylsilyl)ethane 
• 59176-57-7 (Z)-1-phenylthio-1-trimethylsilyl-2-phenylethylene 

Relevant academic research and scientific papers

Strategic Trimethylsilyldiazomethane Insertion into pinB-SR Followed by Selective Alkylations

The insertion of the diazo derivative Me3SiCHN2 into pinB-SR σ bonds (R = Ph, Tol, Bn) allows a direct synthesis of multisubstituted H-C(SR)(Bpin)(SiMe3) compounds. Consecutive base-assisted transformations of HC(S)(B) (Si

A Michael Addition and Peterson Olefination Sequence Using 1-Silylethenyl Sulfides and Sulfoxide

Reaction of organolithiums with a 1-(trimethylsilyl)ethenyl sulfide produces 1,2-bis(trimethylsilyl)-cyclopropanes, while use of 1-silylethenyl sulfides bearing a bulkier silyl moiety results in exclusive formation of the corresponding Michael adducts anions which are then quenched with aldehydes to give vinyl sulfides.On the contrary, a 1-(trimethylsilyl)ethenyl sulfoxide undergoes smooth Michael addition with a variety of organometallics and the resulting carbanion intermediates can be quenched with aldehydes to produce vinyl sulfoxides.Scope and limitations of these sequential reactions are discussed.

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).

ALDEHYDES FROM ALKYLLITHIUMS WITH 2-CARBON HOMOLOGATION

1-Phenylthio-trimethylsilylalkanes, which are readily converted to aldehydes, are prepared by the addition of alkyllithiums to phenylthioethene, trimethylsilylethene and 1-phenylthio-1-trimethylsilylethene.