Thiourea -oxides are labile compounds that suffer from a quick overoxidation when directly prepared from thioureas. Therefore, we have developed an alternative route on the basis of the SO transfer from a thiirane -oxide onto sterically encumbered -heterocyclic carbenes, including imidazole- and imidazoline-ylidenes, and a cyclic alkyl amino carbene. Reaction conditions and DFT computations suggest a concerted SO transfer mechanism. Thiourea -oxides are nucleophiles adding to dimethyl acetylenedicarboxylate under fission of the S-O bond.
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