Regiospecific Functionalization of Dimetalated (1-Naphthyl)acetylene. Efficient Synthetic Procedures for Naphtho[2,1-b]chalcophenes
- 1 September 1989
- journal article
- research article
- Published by Taylor & Francis in Synthetic Communications
- Vol. 19 (15) , 2691-2701
- https://doi.org/10.1080/00397918908053063
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 naphtho[2,1-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.Keywords
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