190672-20-9Relevant academic research and scientific papers
Rh(ii)/phosphine-cocatalyzed synthesis of dithioketal derivatives from diazo compounds through simultaneous construction of two different C-S bonds
Rao, Changqing,Mai, Shaoyu,Song, Qiuling
, p. 5964 - 5967 (2018)
Rhodium(ii)/phosphine-cocatalyzed bis-sulfuration of α-diazocarbonyl compounds using thiosulfonates as the sulfenylating agent, which provided two sulfur-containing moieties, was developed via simultaneous inter- and intra-molecular C-S bond formation. This novel protocol provides a rapid synthetic route to dithioketal derivatives in moderate to good yields in an atom-economic process. The transformation is proposed to proceed through phosphine ylide formation followed by S(O2)-S bond cleavage and rearrangement.
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 new methodology for obtaining α-oxo ester equivalents: Sulfanylation of α-sulfonyl carboxylic esters in a solid/liquid phase transfer catalytic system
Wladislaw, Blanka,Marzorati, Liliana,Junior, Nelson Ferreira Claro,Di Vitta, Claudio
, p. 420 - 422 (2007/10/03)
A new, convenient procedure for the synthesis of a wide range of α-methylsulfanyl-α-phenylsulfonyl carboxylic esters has been developed and their facile conversion to the corresponding α-oxo esters demonstrated.
