134993-85-4

Usage

Common uses

Reagent for preparation of organic compounds, substrate for enzymatic reactions, building block for synthesis of organic molecules, key intermediate in production of pharmaceuticals and agrochemicals, stabilizer and cross-linking agent in production of plastics and polymers

Upstream product

• 66693-06-9 ethyl 2-(benzenesulfonyl)propanate 
• 535-13-7 2-chloro-propanoic acid, ethyl ester 
• 873-55-2 sodium benzenesulfonate 
• 257613-77-7 ethyl 2-(benzenesulfonyl)-2-(phenylseleno)propanate 

Downstream Products

• 145144-87-2 3-Adamantan-1-yl-2-benzenesulfonyl-2-(pyridin-2-ylsulfanyl)-propionic acid ethyl ester 
• 148903-67-7 β-benzoyl-2-methylenepropionic acid methyl ester 
• 145144-75-8 2-Benzenesulfonyl-5-phenyl-2-(pyridin-2-ylsulfanyl)-pentanoic acid ethyl ester 
• 145144-81-6 2-Benzenesulfonyl-3-cyclohexyl-2-(pyridin-2-ylsulfanyl)-propionic acid ethyl ester 

Relevant academic research and scientific papers

[2 + 1] Cycloaddition Reactions of a 1-Seleno-2-silylethene to 2-Sulfonylacrylates: Stereoselective Synthesis of Sulfone-Substituted Cyclopropanes

Reaction of 1-(phenylseleno)-2-(trimethylsilyl)ethene 1 and methyl or ethyl 2-p-toluene- or benzene-sulfonylacrylates 3 in the presence of SnCl4 at -78°C gave sulfone-substituted cyclopropanes 4 as single stereoisomers. The structure of one of these crystalline cyclopropane products was elucidated by X-ray crystallographic analysis. The relative stereochemistry of the cyclopropane ring carbon (C2) and selenosilylmethyl group was determined as R,R and S,S, which is consistent with previous mechanical considerations and the NOE determination. 2-Sulfinyl acrylate 2 did not undergo this cycloaddition. The difference in reactivity of the sulfoxide 2 and sulfones 3 toward 1 was explained by comparison of LUMO levels of 2-SnCl4 and 3-SnCl4 complexes and activation energies in the synclinal addition of 1 to the complexes.