Tetrahedron Letters p. 6185 - 6188 (1986)
Update date:2022-07-30
Topics:
Seyed-Mahdavi, Fereydoun
Teichmann, Stephan
Meijere, Armin de
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.
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