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Synlett 1992; 1992(10): 807-808
DOI: 10.1055/s-1992-21499
DOI: 10.1055/s-1992-21499
letter
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Binaphthothiophene: Source of 1,1′-Binaphthalene, Perylene, 2,2′-Diiodo- and 2,2′-Dimethyl-1,1′-Binaphthalene
Further Information
Publication History
Publication Date:
08 March 2002 (online)
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.