Abstract
Trifluoroacetic anhydride induced Pummerer reactions of carbazole-sulfoxide 1 follow an unusual pathway, in which the initially formed acyloxysulfonium salt 3 undergoes not the usual abstract of α-proton but internal nucleophilic substitution with the indole nuclear followed by S n′-type reaction of an intermediate 4 with additive nucleophiles to give 1-substituted carbazole sulfides 2.
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