Selective Sulfenylative Desulfonylation or Decarbalkoxylation of α-Sulfonyl Malonates with DABCO or Bu3N: Reactivity and Conformational Analysis

…, JCD Lopes, L Marzorati, B Wladislaw

Index: Donnici, Claudio L.; Pereira, Elaine Henriques Teixeira; Lopes, Julio C. Dias; Marzorati, Liliana; Wladislaw, Blanka Synthetic Communications, 2010 , vol. 40, # 3 p. 342 - 350

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Abstract

The study on reactivity of several α-substituted α-sulfonyl 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 α-substituent, because of sterical hindrance around the electrophilic centers (SO2 and CO2R). The derivatives with crowded α-substituents suffer ...