110794-04-2Relevant academic research and scientific papers
A Convenient General Access to Methyl 2-Chloro-2-cyclopropylidenacetates, Reactive Michael Acceptors and Cycloaddends
Liese, Thomas,Teichmann, Stephan,Meijere, Armin de
, p. 25 - 32 (1988)
The reaction of 1-chloro-1-(trichlorovinyl)cyclopropanes 1 with potassium hydroxide/methanol or sodium methoxide/methanol yields trimethyl 2-chloro-2-cyclopropylidenorthoacetates 7, which can be quantitatively converted to the corresponding esters 8 by ac
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.
