Cyclodienyl 1,3-Dianionic Synthons: A Novel Synthesis of 5,5-Dimethyl-1,3-bis-(trimethylsilyl)cyclohexa-1,3-diene and its Diels-Alder [_π4_s+_π2_s] Cycloadditions with Six Dienophiles

摘要

The synthesis of 5,5-dimethyl-1,3-bis(trimethylsilyl)cyclohexa-1,3-diene: a novel eyelie 1,3-dianionic synthon is reported by the Wurtz-Fittig coupling reaction fo 1,3-dichloro-5,5-dimethyleyclohexa-1,3-diene with metallic sodium und chlorotrimethylsilane in anhydrous ether solvent. The compoud on further Diels-Alder [_π4_s+_π2_s] eyelnaddition with five N-substituted maleimides gavefive novel cyclodducts: the N-substituted 11,11-dimethyl-1,8-bis(trimethylsilyl)-4-azatricyclo[5.2.2.0~(2.6)]undee-8-ene-3,5-dinne in 94-97% nverall yields