69358-42-5

Upstream product

• 28403-86-3 1-phenyl-2-(phenylthio)propan-1-one 
• 94-36-0 dibenzoyl peroxide 
• 7205-91-6 phenylthiomethyl chloride 
• 37471-46-8 1-phenyl-1-trimethylsiloxypropene 
• 98-86-2 acetophenone 
• 7205-94-9 chloromethyl phenyl sulfoxide 
• 145663-81-6 1--1-phenylethanol 

Downstream Products

• 769-60-8 2-methyl-1-phenylprop-2-en-1-one 

Relevant academic research and scientific papers

α-Benzoyloxylation of β-keto sulfides at ambient temperature

A facile and efficient protocol for the α-benzoyloxylation of β-keto sulfides is presented. This methodology provides a step-economical, mild and practical access to highly functionalized α-O-benzoyloxy substituted β-keto sulfides, including those with quaternary carbons, which are not easily obtained through currently available methods.

Oxidation of sulfides with N-bromosuccinimide in the presence of hydrated silica gel

An efficient and highly selective procedure for oxidation of sulfides to sulfoxides with N-bromosuccinimide (NBS) in the presence of hydrated silica gel has been developed. Hydrated silica gel supplies the water necessary for decomposition of the intermed

A facile and selective procedure for oxidation of sulfides to sulfoxides on silica gel supported magnesium monoperoxyphthalate (MMPP) in dichloromethane

The scope of the magnesium monoperoxyphthalate (MMPP) oxidation of sulfides to sulfoxides has been extended by using hydrated silica gel as a solid support in dichloromethane media. This procedure works in the presence of a number of functional groups on the sulfides, including carbonyl and alkene groups that have been known to undergo Baeyer-Villiger oxidation and epoxidation with MMPP when using more conventional procedures. To our knowledge, this is the first example of oxidation of sulfides containing a carbonyl group with MMPP in non-aqueous media without any Baeyer-Villiger reaction. The reported procedure is easy to perform, product separation is trivial and it produces excellent yields.

Generation of the α-Sulfinyl Carbenoid from α-Chloro Sulfoxides: A New Method for One-Carbon Homologation of Ketones to α-Sulfinyl Ketones

Treatment of 1-chloroalkyl phenyl sulfoxides with a base gave carbenoids rather than free carbenes.The carbenoids were successfully used in a new method for homologation of ketones to α-sulfinyl ketones.Treatment of the carbanion of chloromethyl phenyl sulfoxide with ketones gave the adducts, α-chloro β-hydroxy sulfoxides, in nearly quantitative yields. the adducts were treated with excess lithium diisopropylamide to give one-carbon homologated α-sulfinyl ketones via α-sulfinyl β-oxido carbenoids in moderate to good yields.This type of reaction was found not to occur with the corresponding sulfones.

α-Sulfinyl carbenoid: One-carbon homologation of ketones to α-sulfinyl ketones using chloromethyl phenyl sulfoxide

Addition of the carbanion of chloromethyl phenyl sulfoxide to ketones gave the adducts, which were treated with lithium diisopropylamide to afford one-carbon homologated α-sulfinyl ketones via α-sulfinyl carbenoids in moderate to high yields.

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.