77873-88-2Relevant articles and documents
THE AdNSNE MECHANISM IN THE REACTION OF PHENOL AND BENZENETHIOL WITH α-BROMO MICHAEL ACCEPTORS IN THE K2CO3-ACETONE SYSTEM
Rosnati, Vittorio,Saba, Antonio,Salimbeni, Aldo,Vettori, Umberto
, p. 249 - 256 (2007/10/02)
In the reaction of α-bromo Michael acceptors with either phenol or benzenethiol formal substitution of the vinylic bromine proceeds through addition of the phenolic reagent, followed by nucleophilic substitution and β-elimination (AdNSNE mechanism) in the system K2CO3-acetone.The process is shown to be stereospecific in the case of 2a,b and 3b,c, leading to the corresponding Z isomer.The reactivity of substrates 1-4 is discussed in terms of their structural features.