116117-96-5

Upstream product

• 63603-28-1 1-methoxy-1-phenyl-2-phenylselenoethane 
• 5707-04-0 Phenylselenyl chloride 
• 100-42-5 styrene 

Downstream Products

• 35050-01-2 α-(phenylseleno)acetophenone 
• 63603-28-1 1-methoxy-1-phenyl-2-phenylselenoethane 
• 98-86-2 acetophenone 
• 113674-98-9 1-methoxy-1-phenyl-2-phenylseleninylethane 
• 3898-26-8 2-chloro-1-phenyl-1-methoxyethane 
• 1074-11-9 1-(1,2-dichloroethyl)benzene 

Relevant academic research and scientific papers

Acetoxyselenenylation of Olefins for the Preparation of Vinylic and Allylic Acetates

Terminal and 1,2-disubstituted olefins were irreversibly acetoxyselenenylated by treatment with PhSeBr in an acetate buffer solution.Styrene derivatives yielded only Markovnikov adducts whereas simple terminal olefins and olefins containing an allylic oxygen substituent (acyloxy or aryloxy group) afforded significant amounts (50-85percent) of the anti-Markovnikov isomer.The product mixtures were isomerized to contain 90-97percent of the Markovnikov products by treatment with a catalytic amount (6-41percent) of BF3*OEt2 in chloroform.Oxidation (SO2Cl2/hydrolysis or MCPBA) of the isomerized products and selenoxide elimination at elevated temperature toward the acetoxy group afforded enol acetates in fair yields.The selenoxides of the anti-Markovnikov isomers (unisomerized mixtures) spontaneously eliminated, in the presence of the selenoxides of the Markovnikov isomer, to give allylic acetates in good yields at ambient temperature.

METHOXYCHLORINATION AND DIMETHOXYLATION OF ALKENES. THE REACTIONS OF SUBSTITUTED STYRENES WITH PHENYLSELENENYL CHLORIDE IN METHANOL

The addition of PhSeCl to α- and β-substituted styrenes in methanol is regio- and stereospecific and affords the products of methoxyselenenylation.These compounds further react with PhSeCl to give the deselenenylation products.In the case of α-substituted styrenes, 1-methoxy, 2-chloroalkanes are produced, whereas with β-substituted styrenes the major reaction products are the 1,2-dimethoxyalkanes and the 2,2-dimethoxyalkanes in which phenyl migration has occured.It is shown that these reactions proceed through the intermediate formation of the alkyl phenylselenium dichlorides, PhCR(OMe)CHR1SeCl2Ph, which evolve with different mechanisms depending on the structure of the starting alkenes.