PERI-BRIDGED NAPHTHALENES. 4. CHALCOGEN-BRIDGED ACENAPHTHYLENES

Article abstract of DOI:10.1016/S0040-4039(00)74552-7

Three new electron donors, acenaphtho<5,6-cd>-1,2-dithiole (1), acenaphtho<5,6-cd>-1,2-diselenole (2), and acenaphtho<5,6-cd>-1,2-ditellurole (3), can be prepared in 28percent, 22percent, and 14percent yields respectively by reaction of the elemental chalcogens (S, Se, Te) with 5,6-dilithioacenaphthylene (4).Compound 4 is generated by treatment of 5,6-dibromoacenaphthylene (5), for which a convenient preparation is described, with n-butyllithium(2 equiv.) in THF at -78 deg C.