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Issue 24, 2012
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Radical-mediated reduction of the dithiocarbamate group under tin-free conditions

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Abstract

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.

Graphical abstract: Radical-mediated reduction of the dithiocarbamate group under tin-free conditions

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Publication details

The article was received on 28 Feb 2012, accepted on 23 Apr 2012 and first published on 15 May 2012


Article type: Paper
DOI: 10.1039/C2OB25434D
Citation: Org. Biomol. Chem., 2012,10, 4752-4758
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    Radical-mediated reduction of the dithiocarbamate group under tin-free conditions

    C. McMaster, R. N. Bream and R. S. Grainger, Org. Biomol. Chem., 2012, 10, 4752
    DOI: 10.1039/C2OB25434D

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