Regiospecific Functionalization of Dimetalated (1-Naphthyl)acetylene. Efficient Synthetic Procedures for Naphtho[2,1-b]chalcophenes |
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| Authors: | Jaap C Hanekamp Peter A A Klusener Lambert Brandsma |
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| Institution: | Department of Synthetic Organic Chemistry , University of Utrecht , Padualaan 8, 3584, CH, Utrecht, The Netherlands |
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| Abstract: | Treatment of (1-naphthyl)acetylene (1) with two mol equivalents of the BuLi-t-BuOK reagent in tetrahydrofuran/hexane, followed by successive addition of anhydrous lithium bromide, sulfur, selenium, or tellurium and t-butylalcohol gives naphtho2,1-b]thiophene, -selenophene and -tellurophene in good yields. Reaction of dimetalated 1 with iodine or dimethyldisulfide afforded 2-iodo-, and 2-thiomethyl(1-ethylnyl)naphthalene. |
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