33697-58-4

Upstream product

• 516-05-2 methyl-propanedioic acid 
• 108-95-2 phenol 
• 60179-38-6 2-methyl-malonic acid monophenyl ester 

Downstream Products

• 15074-17-6 4-hydroxy-3-methyl-2H-chromen-2-one 
• 150056-75-0 4-Hydroxy-3-methyl-6-phenyl-1H-pyridin-2-one 
• 150056-80-7 4-Hydroxy-3,5-dimethyl-6-phenyl-1H-pyridin-2-one 
• 150056-76-1 4-Hydroxy-3-methyl-6-p-tolyl-1H-pyridin-2-one 
• 150056-79-4 6-(4-Chloro-phenyl)-4-hydroxy-3-methyl-1H-pyridin-2-one 
• 150056-77-2 4-Hydroxy-6-(4-methoxy-phenyl)-3-methyl-1H-pyridin-2-one 
• 150056-81-8 4-Hydroxy-3,5-dimethyl-6-p-tolyl-1H-pyridin-2-one 
• 223659-76-5 2-(4-chlorophenyl)-6-hydroxy-5-methylpyrimidin-4(3H)-one 
• 150056-78-3 4-Hydroxy-3-methyl-6-(4-nitro-phenyl)-1H-pyridin-2-one 

Relevant academic research and scientific papers

Selective sulfenylative desulfonylation or decarbalkoxylation of α-sulfonyl malonates with DABCO or Bu3N: Reactivity and conformational analysis

The study on reactivity of severalαsubstituted αsulfonyl malonates toward 1,4-diazabicyclo[2.2.2]octane (DABCO) and Bu3N is described. The reactivity with DABCO revealed the possible competition between decarbalkoxylation and unexpected desulfonylation, depending on the-substituent, because of sterical hindrance around the electrophilic centers (SO2 and CO2R). The derivatives with crowded α-substituents suffer selective desulfonylation, and a novel and efficient desulfonylation method can be proposed. The dependence of the reactivity ofα-sulfonyl malonates on the sterical hindrance around the electrophilic centers is confirmed by conformational analysis (Macromodel/MM2* and Mopac/MP3). The carbanionic mechanism is proved because the corresponding protonated, deuterated, and sulfenylated products were obtained by addition of the corresponding electrophilic agents. Bu3N showed itself to be a novel selective decarbalkoxylation agent for any-substituted-sulfonyl malonate.