Thiacrown

Homolytic addition of dithiols to alkynes as a new approach to construction of dithiacyclanes and thiacrown ethers 97IZV1256. 

Thiacrown ether and related systems also tend to involve octahedrally coordinated rhodium(III) [107]. 

Substituted thiacrown ethers pendent on vinyl polymers [1228]... 

L. V. Minevski and J. A. Gaboury. Thiacrown ether compound corrosion inhibitors for alkanolamine units. Patent EP 962551, 1999. 

Grant GJ (2006) Mercury(II) Complexes with Thiacrowns and Related Macrocyclic Ligands 120 107-141... 

The sulfimide group R2S = NR is isoelectronic with R2S = O, and recent studies have revealed the first examples of macrocyclic derivatives from reaction of the thia crown with MSFI.155,156 These compounds are of interest as ligands in their own right, and also because they provide a means of functionalizing the thiacrown at the S atom and hence the possibility of introducing pendant groups. 

Another interesting application of thiadiazole chemistry is the synthesis of thiacrown ether. To this end, the precursor thiadiazole is treated with K2CO3 in the presence of 1,11-dichloro-3,6,9-trioxaundecane to give l,ll-bis(5-hydroxybenzofuran-2-sulfanyl)-3,6,9-trioxaundecane, which can be transformed into thiacrown ether 110 by treatment with tetraethylene glycol bis-tosylate and bases <00T3933>. 

The unsymmetrical thiacrown porphyrazines Mg[pz(A3B)], where A = Bn, B = S3 (92a) and Mg[pz(A3B)], where A = Bn, B = S4 crown (93a) were formed by a cross-condensation of excess 3,6-dibutyl-1,2-dicyanobenzene and the corresponding thiaether crown dithiomaleonitrile derivative (91). The porphyrazines were demetalated with TFA and remetalated with either copper or nickel acetate to form Compounds 92c, 93c and 93d (16-18%). 

Thia-8-oxoguanosine, 2 823 Thiaboranes, 4 170, 204 preparation, 4 205 Thiacrown ether monomers, 23 707 Thiacrown ether polymer ligands, 23 702 Thiamine, 2 737-738, 25 781, 795-796. 

Synthetically is it relatively challenging to prepare heavier analogues of the thiacrowns containing Se and Te donors. The macrocycle [16] ane-Se4 is known and forms complexes with Ru(II) that can be oxidised to Ru(III) and isolated.24 Tellurium-containing macrocycles are limited to mixed Te/S donors such as [/j]ane-S2Te (n = 9, 11 and 12).25... 

Styryl dyes CESDs 3a-e, 4a-e incorporating thiacrown ether moieties exhibit a strong preference for the formation of complexes with heavy metal salts (Hg2+, Pb2+, Cd2+, Ni2+ or Zn2+perchlorates) [17,18],... 

Saito, K., Masuda, Y., and Sekido, E. (1983) Liquid-liquid extraction of metal ions by the thiacrown compound 1,4,8,11-tctrathiacyclotctradccane, Anal. Chim. Acta, 151(2), 447-455. 

---