Diels-Alder reactions of cyclopentadienones with aryl alkynes to form biaryl compounds.
Diels-Alder reactions of cyclopentadienones, to afford substituted biaryls, were studied using an expanded substrate base. Electron-withdrawing groups on the aryl alkyne dienophile facilitated the reaction, and these substrates gave better yields than those with electron-donating substituents. Steric effects were also found to be important, and o,o'-dimethylphenylacetylene gave much poorer yield of biaryl product.
Department of Chemistry, Case Western Reserve University, Cleveland, Ohio 44106, USA. ajp4@case.edu
Anthony J
AJ
Pearson
Yan
Y
Zhou
D000480:Alkynes / Q000737:chemistry*; D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis*; D003517:Cyclopentanes / Q000737:chemistry*; D011084:Polycyclic Aromatic Hydrocarbons / Q000138:chemical synthesis
D000480:Alkynes; D001643:Bridged Bicyclo Compounds; D003517:Cyclopentanes; D011084:Polycyclic Aromatic Hydrocarbons