82751-11-9Relevant articles and documents
Selective sulfenylative desulfonylation or decarbalkoxylation of α-sulfonyl malonates with DABCO or Bu3N: Reactivity and conformational analysis
Donnici, Claudio L.,Pereira, Elaine Henriques Teixeira,Lopes, Julio C. Dias,Marzorati, Liliana,Wladislaw, Blanka
experimental part, p. 342 - 350 (2010/04/04)
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.
A Convenient Method for Preparation of 2-(Methylthio)alkanoic Acids and Their Related Compounds Using the Carbanions of Substituted Malonic Esters
Ogura, Katasuyuki,Itoh, Hiroshi,Morita, Toshio,Sanada, Kunio,Iida, Hirotada
, p. 1216 - 1220 (2007/10/02)
Starting from alkyl- or aryl-substituted malonic esters prepared by various methods, 2-(methylthio)alkanoic acids are synthesized by successive treatment with sodium ethoxide and with S-methyl methanethiosulfonate, followed by alkaline hydrolysis which causes concurrent decarboxylation.Production of 2-(phenylthio)alkanoic acids is also achieved in a similar manner.
