110794-06-4Relevant academic research and scientific papers
REACTIVITY ENHANCEMENT THROUGH STRAIN AND ELECTRONIC EFFECTS: α-HETEROCYCLOPROPYLIDENACETATES AS POWERFUL MICHAEL ACCEPTORS
Seyed-Mahdavi, Fereydoun,Teichmann, Stephan,Meijere, Armin de
, p. 6185 - 6188 (2007/10/02)
The new α-thiosubstituted cyclopropylidenacetates 2c,d have been synthesized from 2a.The relative reactivities of 2a,b,c,d, their substituted analogues 4a and 3,3-dimethylacrylate (7) towards thiophenolate were determined by competition experiments.Both ring strain and α-heterosubstituents drastically enhance the reactivity. 2c readily undergoes cycloaddition to cyclopentadiene and addition of carbon nucleophiles at room temperature.
