Английская Википедия:Benzene-1,2-dithiol

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Шаблон:Chembox

Benzene-1,2-dithiol is the organosulfur compound with the formula CШаблон:SubHШаблон:Sub(SH)Шаблон:Sub. This colourless viscous liquid consists of a benzene ring with a pair of adjacent thiol groups. The conjugate base of this diprotic compound serves as chelating agent in coordination chemistry and a building block for the synthesis of other organosulfur compounds.[1]

Synthesis

The compound is prepared by ortho-lithiation of benzenethiol using butyl lithium (BuLi) followed by sulfidation:[2]

CШаблон:SubHШаблон:SubSH + 2 BuLi → CШаблон:SubHШаблон:SubSLi-2-Li + 2 BuH
CШаблон:SubHШаблон:SubSLi-2-Li + S → CШаблон:SubHШаблон:Sub(SLi)Шаблон:Sub
CШаблон:SubHШаблон:Sub(SLi)Шаблон:Sub + 2 HCl → CШаблон:SubHШаблон:Sub(SH)Шаблон:Sub + 2 LiCl

The compound was first prepared from 2-aminobenzenethiol via diazotization.[3] Alternatively, it forms from 1,2-dibromobenzene.[4]

Reactions

Oxidation mainly affords the polymeric disulfide. Reaction with metal dihalides and metal oxides gives the dithiolate complexes of the formula LШаблон:SubM(SШаблон:SubCШаблон:SubHШаблон:Sub) where LШаблон:SubM represents a variety of metal centers, e.g. (CШаблон:SubHШаблон:Sub)Шаблон:SubTi. Ketones and aldehydes condense to give the heterocycles called dithianes:

CШаблон:SubHШаблон:Sub(SH)Шаблон:Sub + RR’CO → CШаблон:SubHШаблон:Sub(S)Шаблон:SubCRR’ + HШаблон:SubO

Related compounds

3,4-Toluenedithiol, also called dimercaptotoluene (CAS#496-74-2), behaves similarly to 1,2-benzenedithiol but is a solid at ambient temperatures (m.p. 135-137 °C).

Alkene-1,2-dithiols are unstable, although metal complexes of alkene-1,2-dithiolates, called dithiolene complexes, are well known.[1]

References

Шаблон:Reflist

  1. 1,0 1,1 Karlin, K. D.; Stiefel, E. I., Eds. “Progress in Inorganic Chemistry, Dithiolene Chemistry: Synthesis, Properties, and Applications” Wiley-Interscience: New York, 2003. Шаблон:ISBN
  2. Шаблон:Cite journal
  3. Шаблон:Cite journal
  4. Шаблон:OrgSynth