Dilithiation of 1??benzenesulfonylindoles

RJ Sundberg, R Broome, CP Walters…

Index: Sundberg, Richard J.; Broome, Rita; Walters, Claudia Powers; Schnur, Dora Journal of Heterocyclic Chemistry, 1981 , vol. 18, p. 807 - 809

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Citation Number: 18

Abstract

Abstract Benzenesulfonylindole is converted to a dilithio derivative by 2.2 equivalents of lithiating reagent. The dilithio derivative gives rise to sultones on reaction with carbonyl compounds. This reaction proceeds by an intramolecular displacement of the indole group from the bis-adduct. Fair to poor yields of the 2-indolycarbinols can also be isolated. Benzoyl chloride forms a thiazine dioxide ring by addition at both the 2-indolyl and 2′- ...