55980-76-2

Upstream product

• 64190-24-5 1-cyclobutanol 
• 91525-45-0 1-(Benzenesulfinyl-iodo-methyl)-cyclobutanol 
• 41719-09-9 Iodomethyl phenyl sulfoxide 
• 1208-20-4 S-phenyl benzenethiosulfinate 
• 120-92-3 cyclopentanone 
• 882-33-7 diphenyldisulfane 
• 52190-40-6 2-(phenylthio)cyclopentanone 
• 94-36-0 dibenzoyl peroxide 
• 7205-94-9 chloromethyl phenyl sulfoxide 
• 670-98-4 methyl benzenesulfinate 
• 4972-29-6 benzenesulphinyl chloride 
• 19980-43-9 1-(trimethylsilyloxy)cyclopentene 

Downstream Products

• 34780-08-0 2-(phenylthio)cyclopent-2-en-1-one 
• 98877-48-6 2-cyclopentene-1-on-tosylhydrazone 
• 98877-47-5 2-(phenylsulfinyl)cyclopentanone tosylhydrazone 

Relevant academic research and scientific papers

One-pot synthesis of α-phenylsulfinyl ketones by reaction of phenyl benzenethiosulfinate with enolate anions, and synthesis of sulfoxides and sulfides by its reaction with Grignard reagents

Phenyl benzenethiosulfinate reacts with enolate anions derived from ketones to give α-phenylsulfinyl ketones directly, together with minor amounts of α-phenylsulfanyl ketones. These are easily separated by forming the water-soluble sodium salts of the sulfinyl compounds. Grignard reagents also react with phenyl benzenethiosulfinate, to give mixtures of sulfoxides and sulfides.

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.

Selective and mild oxidation of sulfides to sulfoxides by oxodiperoxo molybdenum complexes adsorbed onto silica gel

Aliphatic and aromatic sulfides, ketosulfides, sulfinyl acids and esters, and olefinic sulfides were oxidized to sulfoxides using oxodiperoxo complexes of molybdenum coated on silica gel (150 ? pore size) in very high yields. Complete chemoselectivity was observed for the oxidation of all functional sulfides. Sulfones were, however, the main products of the reaction when the complexes were not coated on silica gel. The influence of silica gel as the support of these reactions was also investigated and it was demonstrated that it alters the reactivity of the complex but it is not responsible for the excellent chemoselectivity of the complexes. The complex [MoO(O2)2(pyrazole) (H2O)] proved to be more reactive than [MoO(O2)2(Opyr) (H2O)].

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.

Chemoselective Method for the Preparation of Phenyl Sulfoxides by the Oxidation of Phenyl Sulfides with 2-Hydroperoxy-2-methoxypropane

Phenyl sulfoxides are easily prepared by the chemoselective oxidation of the corresponding sulfides with molecular equivalents of 2-hydroperoxy-2-methoxypropane.This reagent is generated from 2,3-dimethyl-2-butene by ozonization in methanol.

Synthesis and Photochemistry of 1-Diazo-2-cyclopentene and 2-Diazobicyclohepta-3,6-diene

A potentially general route to cyclic α,β-unsaturated diazo compounds via enone tosylhydrazones is described.The unsaturated tosylhydrazone is generated by sulfoxide elimination.Syntheses of 2-diazobicyclohepta-3,6-diene and 1-diazo-2-cyclopentene

IODOMETHYL PHENYL SULFOXIDE: REACTIVITY AND SYNTHETIC APPLICATIONS

Lithio iodomethyl phenyl sulfoxides reacted with alkyl halides and carbonyl compounds to give adducts in good to moderate yields.Solvolysis of the carbonyl adducts led to sulfones or the ring expanded product.