51679-33-5

Upstream product

• 107454-82-0 1-(nitromethyl)cyclopentene oxide 
• 930-69-8 sodium thiophenolate 
• 7205-91-6 phenylthiomethyl chloride 
• 19980-43-9 1-(trimethylsilyloxy)cyclopentene 
• 7148-07-4 1-pyrrolidinocyclopent-1-ene 
• 51679-32-4 2-(phenylthiomethyl)cyclohexanone 
• 13865-50-4 methoxymethyl phenyl sulfide 
• 1193-82-4 racemic methyl phenyl sulfoxide 
• 120-92-3 cyclopentanone 
• 2562-42-7 1-nitromethylcyclopentene 
• 43180-39-8 dimethyl<(phenylthio)methyl>amine 
• 936-52-7 1-(N-morpholino)cyclopent-1-ene 

Downstream Products

• 137846-44-7 6-Phenylsulfanylmethyl-1,4-dioxa-spiro[4.4]nonane 

Relevant academic research and scientific papers

Lewis acid mediated selective chalcogenalkylation of silyl enol ethers with [O,S]-acetals

Silyl enol ethers of ketones were selectively alkylated with [O,S]- acetals mediated by Lewis acid in a Mukaiyama type Aldol reaction. The products were β-alkoxy- and/or β-sulfanyl carbonyl compounds depending on the catalyst employed.

α-Sulfenylalkylation of carbonyl compounds at the α-position via magnesium amide-induced enamine sulfenylalkylation with sulfoxides

The reactions of enamines with sulfoxides bearing α-hydrogens in the presence of a magnesium amide, generated in situ from the reaction of ethylmagnesium bromide with diisopropylamine, afforded the corresponding α-sulfenylalkylated ketones and aldehydes in isolated yields ranging from 39 to 76%. This procedure was successfully extended to the bis(methylthio)methylation with methyl (methylthio)methyl sulfoxide.

Carbonyl-Protected β-Lithio Aldehydes and Ketones via Reductive Lithiation. A General Preparative Method for Remarkably Versatile Homoenolate Equivalents

A general procedure for producing homoenolate equivalents consists of reductive lithiation, induced by 4,4'-di-tert-butylbiphenylide, of carbonyl-protected β-(phenylthio) carbonyl compounds prepared in turn by thiophenol addition to enones or the alkylati

Selective Base-Catalyzed Rearrangement of Epoxides into Ketones. Application to γ-Keto Sulfide Synthesis

A methodology for the selective base-catalyzed isomerization of certain epoxides having a β-proton into ketones is presented. β,γ-Epoxy nitro compounds were the substrates for this transformation and underwent a multistep reaction consisting of epoxide ri

α-ALKYLATION AND α-ALKYLIDENATION OF CARBONYL COMPOUNDS BY O-SILYLATED ENOLATE PHENYLTHIOALKYLATION

For many reactions next to a carbonyl group, the use of O-silylated enolate chemistry offers improvements in yield and selectivity over the corresponding reactions of Group I metal enolates.In the case of α-alkylation of carbonyl compounds, Lewis acid (TiCl4 or ZnBr2) promoted phenylthioalkylation of O-silylated enolates 3 by α-chlorosulphides 4 (R3=H, Me, Prn, Pri, Bui, and Me3Si), followed by reductive sulphur removal by Raney nickel, 5->6, is found to be a reliable method for this synthetically important C-C bond forming step.An alternative sulphur elimination pathway via the sulphoxide, 5->7, allows the regio- and stereocontrolled α-alkylidenation of carbonyl compounds.The phenylthioalkylation reaction is applicable to ketones, aldehydes, esters, and lactones.