- Insertion of arynes into thioureas: A new amidine synthesis
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Arynes, generated from trimethylsilyl phenyltriflate precursors, have been found to react with thioureas via a formal π-insertion into the C=S bond. The reaction contrasts with that of ureas, which proceeds via benzyne σ-insertion into the C-N bond, and r
- Biswas, Kallolmay,Greaney, Michael F.
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supporting information; experimental part
p. 4946 - 4949
(2011/11/06)
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- Thiocarbamoylation of amine-containing compounds 5. The mechanism of reactions of tetramethylthiuram disulfide with aliphatic amines
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Thiocarbamoylation of aliphatic amines with tetramethylthiuram disulfide (TMTD) was studied. The reactions were established to proceed according to a two-stage mechanism. In the first stage, S-(thiocarbamoyl)thiohydroxylamines and dimethyl dithiocarbamates are formed. The latter exist in equilibrium with dimethyldithiocarbamic acid, which can undergo decomposition to give dimethylamine and carbon disulfide. In the second stage, several competitive transformations of these intermediates into the final products occur, viz., (1) the reactions of CS2 with primary amines on heating (70-110 deg C) yield mixed and symmetrical thioureas and the reactions of CS2 with secondary amines give symmetrical dithiocarbamates, and (2) insertion of CS2 into S-(thiocarbamoyl)thiohydroxylamines affords thiuram disulfides. Thiuram disulfides formed from primary amines decompose to give isothiocyanates, which are converted into thioureas by condensation with amines, whereas thiuram disulfides which are obtained in the reactions with secondary amines and which cannot form thioureas react with amines analogously to TMTD.
- Boi, Luu Van
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p. 335 - 343
(2007/10/03)
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- Thiocarbamoylation of amine-containing compounds 4. Reactions of tetramethylthiuram disulfide with aliphatic amines
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Thiocarbamoylation of primary and secondary aliphatic amines with tetramethylthiuram disulfide in various solvents at different temperatures was studied. At 110 °C, the reactions with primary amines afforded mixed N,N-dimethyl-N′-alkyl(cycloalkyl)thiourea
- Van Boi, Luu
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p. 2294 - 2298
(2007/10/03)
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