Free radical reaction between 2-benzoyl-1,4-benzoquinones and 1,3-dicarbonyl compounds.
A manganese(III)-mediated reaction between 2-benzoyl-1,4-benzoquinones and 1,3-dicarbonyl compounds that produces benzo[c]furan-4,7-diones and anthracene-1,4-diones with high chemoselectivity is described. With ethyl butyrylacetate, by changing the solvent, benzo[c]furan-4,7-diones and anthracene-1,4-diones can be generated in high chemoselectivities. With ethyl benzoylacetate, N ,N-dimethyl acetoacetamide and 1,3-diones, benzo[c]furan-4,7-diones were produced effectively with high selectivity. With 2-alkyl-5-benzoyl-1,4-benzoquinones, the regioselectivity of this reaction was also studied and the corresponding benzo[c]furan-4,7-dione and anthracene-1,4-dione derivatives were obtained in high regioselectivity.
Chen
Kuang-Po
KP
Department of Chemistry, National Cheng Kung University, Tainan, Taiwan 70101, Republic of China.
Lee
Hen-Qun
HQ
Cheng
Yu-Chih
YC
Chuang
Che-Ping
CP