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Christopher Beattie and Prof. Michael North Titanium(salen)-Catalysed Synthesis of Di- and Trithiocarbonates from Epoxides and Carbon Disulfide ChemCatChem 6

Version of Record online: 12 MAR 2014 | DOI: 10.1002/cctc.201400005

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Salen away on a kinetic sea: The combination of [Ti(salen)O]2 and tetrabutylammonium bromide or tributylamine catalyzes the addition of carbon disulfide to epoxides to form predominantly dithiocarbonates. Ten examples are reported that give the dithiocarbonates in 33–99 % isolated yield. A mechanistic study based on reaction kinetics, stereochemistry, and NMR spectra of reaction mixtures allow a catalytic cycle to be proposed.

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