98-77-1Relevant articles and documents
The β Form of Piperidinium 1-Piperidinecarbodithioate
Wahlberg, Anders
, p. 2099 - 2103 (1980)
+-, 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.
Cu-mediated one-pot three-component synthesis of 3-N-substituted 1,4,2-benzodithiazine 1,1-dioxide derivatives
Dong, Wei,Ge, Zemei,Wang, Xin,Li, Ridong,Li, Runtao
, (2020/07/03)
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.
Cyclic ammonium salts of dithiocarbamic acid: stable alternative reagents for the synthesis of S-alkyl carbodithioates from organyl thiocyanates in water
Biswas, Kinkar,Ghosh, Sujit,Ghosh, Pranab,Basu, Basudeb
, p. 361 - 376 (2016/07/23)
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.
Glycosyl dithiocarbamates: β-selective couplings without auxiliary groups
Padungros, Panuwat,Alberch, Laura,Wei, Alexander
, p. 2611 - 2624 (2014/04/17)
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.
