Reaction of 2-lithio-3,4-bis(trifluoromethyl)furan with electrophiles

Article abstract of DOI:10.1016/S0022-1139(00)80121-9

2-Substituted-3,4-bis(trifluoromethyl)furans are obtained in good yield by treatment of the corresponding 2-lithiofuran with the appropriate electrophile.With methyl acrylate, initial attack occurs at carbonyl carbon but the resulting ketone (R=COCH=CH2) undergoes Michael addition with an excess of the lithium salt.From the reaction with dichloromaleic anhydride, 5,5-bis<3,4-bis(trifluoromethyl)-2-furyl>-3,4-dichloro-2-furanone is formed in 85 percent yield.