- The β Form of Piperidinium 1-Piperidinecarbodithioate
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+-, monoclinic, P21, with a = 12.395(2), b = 15.459(2), c = 14.320(2) Angstroem, β = 93.35(2) deg, Z = 8, V = 2739.3 Angstroem3, Dx = 1.195 Mg m-3.The non-centrosymmetric structure has been refined to R(F2) = 0.110 for 4991 reflexions and 892 parameters.The structure is built up of two independent dimers with pseudo symmetry 2/m.Each pseudocentrosymmetric dimer is composed of two cations and two anions connected by eight N-H...S hydrogen bonds (of which one is weak in one of the dimers).The dimers are packed at van der Waals distances.
- Wahlberg, Anders
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- Cu-mediated one-pot three-component synthesis of 3-N-substituted 1,4,2-benzodithiazine 1,1-dioxide derivatives
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A novel and efficient copper-catalyzed one-pot procedure for the synthesis of 3-N-substituted 1,4,2-benzodithiazine 1,1-dioxide derivatives from 2-halobenzenesulfonamides, amines and CS2 is described. The reaction proceeds through Ullmann-type S-arylation, intramolecular addition of NH2 with C[dbnd]S and dehydrosulfide, which provides a new and useful strategy for construction of cyclic aromatic sulfonamides.
- Dong, Wei,Ge, Zemei,Wang, Xin,Li, Ridong,Li, Runtao
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- A catalyst-free 1,4-Michael-type reaction of in situ generated ortho-quinone methides (o-QMs) with dithiocarbamic acid salts in water
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Abstract: A catalyst-free conjugate addition of dithiocarbamic acid salts to in situ generated ortho-quinone methides (o-QMs) was investigated for the first time. Several dithiocarbamate derivatives of 4-hydroxycoumarine, 4-hydroxypyrone and 2-naphthol were synthesized in moderate-to-good yields in water at room temperature. Graphical abstract: [Figure not available: see fulltext.] Catalyst-free addition of dithiocarbamic acid salts to in situ generated o-QMs in water at room temperature.
- Aryanasab, Fezzeh,Shabanian, Meisam
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p. 1703 - 1713
(2019/04/17)
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- Cyclic ammonium salts of dithiocarbamic acid: stable alternative reagents for the synthesis of S-alkyl carbodithioates from organyl thiocyanates in water
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ABSTRACT: Carbodithioate esters are important functional organosulfur compounds widely used in diverse fields such as pharmaceuticals, agrochemicals and material sciences. Common preparative methods include reaction of alkyl halides, carbon disulfide and bases under both metal-free and metal-catalyzed conditions. However, organyl thiocyanates have not been previously explored, possibly because of their conversion to organyl disulfides under basic conditions. Here, we report an efficient and practical method for the preparation of libraries of carbodithioate esters from organyl thiocyanates by reacting with cyclic amine-based dithiocarbamic acid salts in water. The protocol is found to be applicable in general to various thiocyanates such as benzyl/aroyl methyl/cinnamyl and so on. Other notable features include no by-products such as disulfides, metal- and alkali-free, aqueous conditions, and finally easy and near-quantitative formation of cyclic amine-based dithiocarbamic acid salt as a stable alternative reagent.
- Biswas, Kinkar,Ghosh, Sujit,Ghosh, Pranab,Basu, Basudeb
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p. 361 - 376
(2016/07/23)
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- Investigation of the reaction of dithiocarbamic acid salts with trimethyl orthoformate and styrene epoxide
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The reaction of dithiocarbamic acid salts with trimethyl orthoformate in the presence of BF3·OEt2 was investigated to give 4-(N,N-dialkyldithiocarbamato)-2-dialkyliminio-1,3-dithietane tetrafluoroborates in good yields. Additionally, a one-pot procedure for the synthesis of 2-iminium-1,3-dithiolanes from the BF3·OEt2 catalyzed reaction of dithiocarbamic acid salts with styrene epoxide is described.
- Ziyaei Halimehjani, Azim,Hajilou Shayegan, Mojtaba,Poshteh, Shiva Shakori,Amani, Vahid,Notash, Behrouz,Hashemi, Mohammad M.
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supporting information
p. 7124 - 7127
(2015/12/05)
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- Glycosyl dithiocarbamates: β-selective couplings without auxiliary groups
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In this article, we evaluate glycosyl dithiocarbamates (DTCs) with unprotected C2 hydroxyls as donors in β-linked oligosaccharide synthesis. We report a mild, one-pot conversion of glycals into β-glycosyl DTCs via DMDO oxidation with subsequent ring opening by DTC salts, which can be generated in situ from secondary amines and CS2. Glycosyl DTCs are readily activated with Cu(I) or Cu(II) triflate at low temperatures and are amenable to reiterative synthesis strategies, as demonstrated by the efficient construction of a tri-β-1,6-linked tetrasaccharide. Glycosyl DTC couplings are highly β-selective despite the absence of a preexisting C2 auxiliary group. We provide evidence that the directing effect is mediated by the C2 hydroxyl itself via the putative formation of a cis-fused bicyclic intermediate.
- Padungros, Panuwat,Alberch, Laura,Wei, Alexander
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p. 2611 - 2624
(2014/04/17)
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- Investigation of the reaction of dithiocarbamic acid salts with aromatic aldehydes
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A reaction of dithiocarbamic acid salts with carbonyl compounds was investigated for the first time in the presence of BF3?OEt 2. The reaction is temperature dependent and gives gem-bis(dithiocarbamates) at 35-45 °C as a molecule with high equivalents of dithiocarbamate groups. At lower temperatures (15-20 °C), the 2-iminium-1,3-dithietane is obtained as the only product. The structure of a 2-iminium-1,3-dithietane was accomplished by X-ray crystallographic analysis.
- Ziyaei Halimehjani, Azim,Hajiloo Shayegan, Mojtaba,Hashemi, Mohammad Mahmoodi,Notash, Behrooz
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supporting information; experimental part
p. 3838 - 3841
(2012/10/08)
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- A stable acyclic ligand equivalent of an unstable 1,3-dithiol-5-ylidene
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Substitutes you can rely on: Mesoionic carbenes (MICs) are not always stable. However, the acyclic ethynylcarbamodithioate 2 formed (instead of the corresponding MIC) by deprotonation of dithiolium salt 1 underwent cyclization to its precursor under acidic conditions and reacted with a variety of transition-metal centers to yield robust MIC complexes 3; (see scheme; Tipp=2,4,6-triisopropylphenyl). Copyright
- Ung, Gael,Mendoza-Espinosa, Daniel,Bouffard, Jean,Bertrand, Guy
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supporting information; experimental part
p. 4215 - 4218
(2011/07/07)
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- Bis(1,3-dithiole-2-chalcogenones) and tetrathiafulvalenes in the synthesis of bridged tetrathiafulvalene-containing structures
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Bis(1,3-dithiole-2-chalcogenones) in which the 1,3-dithiole fragments are linked through various bridging groups were synthesized by different methods. Some of these compounds were converted into substituted tetrathiafulvalenes with bridged 1,3-dithiole rings. The same structures were synthesized from preliminarily prepared symmetric tetrathiafulvalenes containing 2-cyanoethylsulfanyl groups in both 1,3-dithiole rings. Similar spacers were used to bridge two tetrathiafulvalene fragments. Syntheses of the involved initial compounds were described.
- Abashev,Bushueva,Lebedev,Shklyaeva
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p. 135 - 147
(2007/10/03)
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- Technetium or rhenium complexes, radiopharmaceutical products comprising them
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The invention relates to a technetium or rhenium complex of formula (I): [in-line-formulae][M (R1CS3)2L]??(I) [/in-line-formulae] in which M is Tc or Re, R1 represents an alkyl, cycloalkyl, aralkyl or aryl group which is unsubstituted or substituted by one or more substituents chosen from halogen atoms, the hydroxyl group, alkyl groups and alkoxy groups, and L is a dithiolate ligand, with the exception of the ligand of formula R2CS2 in which R2 is identical to R1. The dithiolate ligand is preferably a dithiocarbamate. The invention also relates to a radiopharmaceutical product comprising a complex of formula (I) with M representing 99Tc, 186Re or 188Re.
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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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- Photochemical and Thermal Transformations of S-Benzoyl-O-alkyl Xanthates
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The reaction of benzoyl chloride with different potassium-O-alkyl xanthates (n-propyl, iso-propyl, n-butyl) around 0 deg C afforded good yields of corresponding S-benzoyl-O-alkyl xanthates.The structure of these aroyl xanthates were consistent with the spectral data.Aroyl xanthates have been reported to be resistant to photolysis.It has, however, been observed in the present investigation that the fragmentation of these S-benzoyl-O-alkyl xanthates does occur on prolonged photolysis.Irradiation of these xanthates in benzene solution with mercury lamp for 60-70 hr resulted in the formation of benzoyl disulfide.Thermal decomposition around 250 deg C for 15 min gave benzoyl disulfide, corresponding ester and carbon disulfide.
- Darji, R. R.,Shah, A.
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p. 657 - 659
(2007/10/02)
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- INVESTIGATION IN THE FIELD OF BIACETYLENE DERIVATIVES. XLII. ADDITION OF AMMONIUM DITHIOCARBAMATES TO BIACETYLENE
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A simple method was developed for the production of cis-1-buten-ynyl dialkyldithiocarbamates and 1,4-bis(dialkylthiocarbamoylthio)-1,3-butadienes by the reaction of biacetylene and carbon bisulfide in the presence of secondary amines without a catalyst in protic and aprotic solvents.
- Sokolyanskaya, L. V.,Vavilova, A. N.,Volkov, A. N.,Trofimov, B. A.
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p. 2025 - 2028
(2007/10/02)
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