The Attempted Generation of 3,4-Didehydrofuran

4-Trimethylsilyl-3(2H)-furanone ( 4 ) was converted to 4-trimethylsilyl-3-furyl triflate ( 5 ). An attempted generation of 3,4-didehydrofuran ( 3a ) from 5 was unfruitful. On the other hand, 3,4-bis(trimethylsilyl)furan ( 6 ) was also converted to 4-trimethylsilyl-3-furylphenyliodonium triflate ( 7c ) and its fluoride-promoted elimination pathway might involve a biradical intermediate 3b .