Synthese von 5-Methylthio-2-thioxo-1,3-dithiol-4-carbonsäureamiden und -thiolestern, 3-Alkyl-5-bis(alkylthio)methylen-2-thioxo-1,3-thiazol-4(5 H)-onen sowie Röntgenkristallstrukturanalyse des 5-Methylthio-2-thioxo-1,3-dithiol-4-carbonsäure-(N-methyl-anilids) / Synthesis of 5-Methylthio-2-thioxo-1,3-dithiole-4-carboxamides and -thiolesters, 3-Alkyl-5-bis(alkylthio)methylene-2-thioxo-1,3-thiazole-4(5 H)-ones, and X-ray Analysis of 5-Methylthio-2-thioxo-1,3-dithiole-4-carboxyl N-methyl-anilide

Abstract

5-Methylthio-2-thioxo-1,3-dithiole-4-carboxamides (2a–e), the methyl 5-methylthio-2-thioxo-1,3-dithiole-4-carboxythiolate (9), and 3-alkyl-5-bis(alkylthio)methylene-2-thioxo-1,3-thiazole-4(5 H)-ones (4a–f) are obtained by reaction of the corresponding N-substituted ethylxanthogen-acetamides (1, 3, 6) with carbon disulfide under basic conditions followed by alkylation. 5-Methylthio-2-thioxo-1,3-dithiole-4-carboxyl N-methyl-anilide (2d) was characterized by an X-ray crystal structure determination (space group P 1̄, a = 877.3(1), b = 1111.1(2), c = 837.6(1) pm, α = 104.22(2), β = 110.41(1), γ = 69.64(2)°, Ζ = 2, R = 0.039 for 1746 observed unique reflections). The α-oxoketene dithioacetal moiety of the molecule exhibits a noticeable derivation from planarity by a twist of the carbonyl group out of the ethylene plane and shows a short intramolecular S ··· O contact of 277.1 (3) pm.