57205-24-0

Upstream product

• 5707-04-0 Phenylselenyl chloride 
• 502-49-8 cycloactanone 
• 78998-73-9 2-(phenylseleno)-1-cyclooctanol 
• 1666-13-3 diphenyl diselenide 
• 50338-42-6 (E)-1-trimethylsilyloxy-1-cyclooctene 
• 71098-88-9 N-phenylselanylphthalimide 
• 931-88-4 cis-Cyclooctene 

Downstream Products

• 57205-26-2 2-Phenylseleno-2-cycloocten-1-on 
• 104755-28-4 (1-oxo-2-cyclooctanyl)-phenylselenium dichloride 

Relevant academic research and scientific papers

K2S2O8-promoted C-Se bond formation to construct α-phenylseleno carbonyl compounds and α,β-unsaturated carbonyl compounds

A novel K2S2O8-promoted C-Se bond formation from cross-coupling under neutral conditions has been developed. A variety of aldehydes and ketones react well using K2S2O8 as the oxidant in the absence of catalyst and afford desired products in moderate to excellent yields. This protocol provides a very simple route for the synthesis of α-phenylseleno carbonyl compounds and α,β-unsaturated carbonyl compounds.

N-(Phenylseleno)Phthalimide: A Useful Reagent For The α-Selenylation Of Ketones And Aldehydes.

Α-phenylselenoketones and α-phenylselenoaldehydes are obtained with a good regioselectivity by treatment of the corresponding ketones or aldehydes with N-(phenylseleno)phthalimide and p-toluenesulfonic acid. - Key words: Ketones, α-phenylselenoketones, N-

New Mild Methodology for the Synthesis of α-Phenylthio and α-Phenylseleno Ketones

Treatment of trimethylsilyl enol ethers with the adduct 1, derived from chloramine-T and (PhS)2, gave good yields of α-phenylthioketones.The selenium version of this reagent 2 gave α-phenylselenoketones.

Methods for the introduction of a Phenylselenium Dichloride Group into he α-position of Carbonyl Compounds. Syntheses of Enones.

Phenylselenium trichloride, PhSeCl3, direcly introduced, in fair yield, a PhSeCl2 group into the α-position of ketones with loss of HCl.To some extent, depending on the substrate, this reagent was also shown to act as a chlorinating agent toward ketones, yielding α-chloro ketones and α-phenylselenenyl ketones.The latter compounds were readily converted to selenium(IV) dichlorides by SO2Cl2 chlorination to significantly improve the overall yields of the selenetion process.The consecutive treatment of ketones with PhSeCl and SO2Cl2 could also be used for the introduction of a PhSeCl2 group, but this procedure was usually less efficient than the PhSeCl3-based one.Unsymmetrical ketones were selenated with poor regiocontrol.Aldehydes were primarily chlorinated by treatment with PhSeCl3, but consecutive treatment with PhSeCl3 and SO2Cl2 introduced a PhSeCl2 group into the α-position.Carboxylic acids and esters were ureactive toward PhSeCl3 and PhSeCl.PhSeCl3 underwent addition reactions with enones to introduce a PhSeCl2 group α or β to the carbonyl group, depending on the substrate.The carbonyl compounds substituted in the α-position with a PhSeCl2 group were easily converted to the corresponding α,β-unsaturated carbonyl compounds after hydrolysis/selenoxide elimination.Since the selenium(IV) intermediates involved were highly crustalline and easy to purify, the preparation of enones from symmetrical ketones via PhSeCl2 introduction/hydrolytic elimination was especially convenient to perform from the operational point of view.

Oxidation of Alcohols with tert-Butyl Hydroperoxide and Diaryl Diselenide

Treatment of alcohols with tert-butyl hydroperoxide in the presence of diaryl diselenide in refluxing benzene gives the corresponding aldehydes or ketones.Although some allylic alcohols undergo oxidation in the presence of 10-15 mol percent of bis(p-chlorophenyl) diselenide, use of 0.5 equiv of bis(2,4,6-trimethylphenyl) diselenide gives satisfactory results in almost all cases.The procedure can be used for selective oxidation of alcohols bearing a phenylthio or phenylseleno group, which usually survives the reaction conditions to give the corresponding carbonyl compounds.

SELECTIVE OXIDATION OF HYDROXY GROUPS OF PHENYLTHIO AND PHENYLSELENO ALCOHOLS

Various kinds of alcohols bearing phenylthio or phenylseleno moiety were converted into the corresponding carbonyl compounds in good to excellent yields by treating with dimesityl diselenide and tert-butyl hydroperoxide.