Radical-mediated reduction of the dithiocarbamate group under tin-free conditions.

Claire McMaster, Robert N. Bream, Richard S. Grainger

Research output: Contribution to journalArticlepeer-review

34 Citations (Scopus)


Reductive desulfurisation of dithiocarbamates is conveniently achieved using H3PO2–Et3N–ACCN in refluxing dioxane. Fused and spirocyclic β-lactams, prepared through 4-exo trig carbamoyl radical cyclisation–dithiocarbamate group transfer reactions, are reduced without fragmentation of the strained 4-membered ring. Diethyl tetraacetyl-D-glucopyranosyl dithiocarbamate is selectively reduced with or without acyloxy group migration depending on reaction conditions and choice of reductant. Deuterium incorporation from D3PO2–Et3N is observed for a system involving a nucleophilic radical intermediate, but not in the case of the electrophilic radical obtained through acyloxy group migration on a glucose derivative.
Original languageEnglish
Pages (from-to)4752-4758
JournalOrganic and Biomolecular Chemistry
Issue number24
Early online date15 May 2012
Publication statusPublished - 28 Jun 2012


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