Lewis acid-induced rearrangement of 2,3-epoxy sulfides: Regiospecific nucleophilic trapping of thiiranium ion intermediates with nitrogen nucleophiles

Duncan M. Gill, Neil A. Pegg, Christopher M. Rayner

Research output: Contribution to journalArticle

18 Citations (Scopus)


The Lewis acid-induced isomerisation of 2,3-epoxy sulfides into the corresponding 3-trimethylsilyloxy-1,2-thiiranium ions is described. Such intermediates react with nitrogen nucleophiles regiospecifically to form 1-substituted 3-hydroxy 2-thioethers in good to moderate yields with full stereochemical control.

Original languageEnglish
Pages (from-to)1371-1372
Number of pages2
JournalJournal of the Chemical Society, Perkin Transactions 1
Issue number13
Publication statusPublished - 1 Dec 1993
Externally publishedYes


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