93249-25-3

Upstream product

• 15678-99-6 N-tert-butylchloroacetamide 
• 515-42-4 sodium phenylsulfonate 
• 3959-23-7 benzenesulfonylacetic acid 
• 1360789-21-4 2-(phenylsulfonyl)-1-(2,2,6,6-tetramethylpiperidin-1-yl)ethanone 
• 75-64-9 tert-butylamine 

Relevant academic research and scientific papers

Switching pathways: Room-temperature neutral solvolysis and substitution of amides

Stick or twist: By introducing steric hindrance at the nitrogen atom, stable linear amides bearing an electron-withdrawing α-substituent (Z=Ar, PhSO2, P(O)(OR)2, CN, or CO2R) can be induced to undergo solvolysis and substitution reactions through an elimination-addition mechanism (see picture). Key to this process is a low barrier to rotation around the amide bond and the α-substituentZ. Copyright

Reaction of different α-sulfonyl acetamides with methyl acrylate

The base-induced tandem-coupling/cyclization reactions of various α-sulfonyl acetamide derivatives A with methyl acrylate differentiated between two different pathways to form α-sulfonyl analogs of glutarimides B and 2-hydroxycyclohexenecarboxylic acid derivatives C in different ratios. The reaction of α-sulfonyl acetamide dianion with methyl acrylate depended on three factors: the stability of the dianion, concentration of methyl acrylate and the structure of sufonyl and amide substituents. By changing the reaction conditions, we efficiently controlled the cycloaddition reaction to synthesize the desired product, each of which has potential biological activities. A ring closure mechanism is proposed for the reactions.