Benzothiophene Chemistry. VII. Substitution Reactions of 5-Hydroxy-and 5-Aminobenzothiophene Derivatives

FG Bordwell, H Stange

文献索引：Bordwell; Stange Journal of the American Chemical Society, 1955 , vol. 77, p. 5939,5943

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被引用次数: 28

摘要

Electrophilic substitution in 5-hydroxy-, 5-acetamido-, and 5-aminobenzothiophene was found to occur at the 4-position, This is analogous to the behavior of similarly substituted naphthalene derivatives. Unlike 2-naphthol, 5-hydroxybenzothiophene undergoes reactions at both positions ortho to the hydroxyl group under nearly the same conditions. When the sulfur atom in benzothiophene is oxidized to the sulfone stage, orientation in the benzene ...