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18.2.6.1.4.4 Variation 4: Synthesis of Thiocarbamates

DOI: 10.1055/sos-SD-018-00070

Braverman, S.; Cherkinsky, M.; Birsa, M. L.Science of Synthesis, (200518181.

Reaction of lithium dialkylamides with carbon monoxide provides highly reactive dialkylcarbamoyllithium compounds 344 that react at low temperature with carbon disulfide as thiophiles, affording the corresponding thiocarbamates 345, together with the polymer of carbon monosulfide (Scheme 175).[‌168‌] This is in contrast to the reaction with carbonyl sulfide, where the carbamoyllithium compounds attack the carbon atom.

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