72653-52-2

Upstream product

• 108-94-1 cyclohexanone 
• 7210-80-2 neopentyl phenyl sulphide 
• 6651-36-1 1-(Trimethylsilyloxy)cyclohexene 
• 72653-49-7 1-chloro-2,2-dimethylpropyl phenyl sulphide 

Downstream Products

• 72653-53-3 2-(2,2-dimethylpropyl)cyclohexanone 
• 119704-14-2 (E)-2-(2,2-dimethylpropylidene)cyclohexanone 

Relevant academic research and scientific papers

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.

α-Alkylation and α-alkylidenation of carbonyl compounds: Lewis acid-promoted phenylthioalkylation of o-silylated enolates

The O-silylated enolates of ketones, aldehydes, esters, and lactones can be phenylthioalkylated in the presence of Lewis acids; reductive or oxidative sulphur-removal gives the regiospecifically α-alkylated or alkylidenated carbonyl compounds.