1,5-Dithiacyclooctane

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1,5-Dithiacyclooctane
DTO.png
Names
Preferred IUPAC name
1,5-Dithiocane
Other names
DTO
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C6H12S2/c1-3-7-5-2-6-8-4-1/h1-6H2
    Key: QQMWBFKOHYFXKQ-UHFFFAOYSA-N
  • C1CSCCCSC1
Properties
C6H12S2
Molar mass 148.28 g·mol−1
Appearance colorless liquid
Melting point −15 °C (5 °F; 258 K)
Boiling point 245–6 °C (473–43 °F; 518–279 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

1,5-Dithiacyclooctane (DTCO) is an organosulfur compound with the formula (CH2CH2)CH2S)2. This cyclic dithioether is a colorless oil that is soluble in polar solvents. It forms a variety of transition metal thioether complexes.

DTO can be oxidized to the bicyclic dication.[1]

Structure of (DTCO)PdCl2.

DTCO was first prepared in 4% yield by dialkylation of 1,3-propanedithiol with 1,3-dibromopropane.[2]

References[edit]

  1. ^ Musker, W. Kenneth (1992). "Coordination Chemistry of Bidentate Medium Ring Ligands (Mesocycles)". Coordination Chemistry Reviews. 117: 133–57. doi:10.1016/0010-8545(92)80022-J.
  2. ^ Meadow, J. R.; Reid, E. E. (1934). "Ring compounds and polymers from polymethylene dihalides and dimercaptans". J. Am. Chem. Soc. 56 (10): 2177–2180. doi:10.1021/ja01325a058.