Binaphtothiophene: Source of 1,1'-Binaphtalene, Perylene, 2,2 -Diiodo - and 2,2'-Dimethyl-1,1'-Binaphtalene

Binaphthothiophene 2 can be used as a source of 1,1?-binaphthalene and perylene depending on the reaction conditions. For example, reaction of 2 with lithium metal in THF for 45 min followed by the quenching with proton sources (water or alcohols) provides 1,1?-binaphthalene 3. Longer times (ca. 8 h) lead to perylene 4. Quenching with electrophiles other than the proton leads either to 2,2?-disubstituted-1,1?-binaphthalenes or to dihydroperylene derivatives. For example, quenching with iodine or methyl iodide affords the 2,2?diiodo- and the 2,2?-dimethyl-derivatives 5 and 6 which are precursors to several other useful 2,2?-disubstituted-1,1?-binaphthalenes.