Generation and trapping reactions of 1-tert-butoxycarbonyl-3,4-didehydro-1H-pyrrole

The existence of 1-tert-butoxycarbonyl-3,4-didehydro-1H-pyrrole (4) as a reactive and highly strained cyclic cumulene at room temperature has been verified by trapping reaction with benzene, furan and acrylonitrile. The experiment used 3,4-bis(trimethylsilyl)-1'H'-pyrerole to generate 4. The experiment is expected to lead to the future generation of 3,4-didehydrofuran, the group's last and most difficult member to synthesize.