page_title: Xanthate
section_title: Reactions
hierarchical_section_title: Xanthate / Reactions
caption_attribution_description: English: structure of typica metal tris(xanthate) complex
context_page_description: Xanthate usually refers to a salt with the formula ROCS⁻
  ₂M⁺
  , thus O-esters of dithiocarbonate. The name xanthates is derived from Greek ξανθός xanthos, meaning “yellowish, golden”, and indeed most xanthate salts are yellow. They were discovered and named in 1823 by Danish chemist William Christopher Zeise. These organosulfur compounds are important in two areas: the production of cellophane and related polymers from cellulose and for extraction of certain ores. They are also versatile intermediates in organic synthesis. Xanthates also refer to esters of xanthic acid. These esters have the structure ROCSR′.
context_section_description: Xanthate salts characteristically decompose in acid:
  ROCS₂K + HCl → ROH  +  CS₂  +  KCl
  This reaction is the reverse of the method for the preparation of the xanthate salts.  The intermediate in the decomposition is the xanthic acid, ROC(S)SH, which can be isolated in certain cases.
  Xanthate anions also undergo alkylation to give xanthate esters, which are generally stable:
  ROCS₂K  +  R′X   →   ROC(S)SR′  +  KX
  The C-O bond in these compounds are susceptible to cleavage by the Barton–McCombie deoxygenation, which provides a means for deoxygenation of alcohols.
  They can be oxidized to the so-called dixanthogens:
  2 ROCS₂Na + Cl₂  →  ROC(S)S₂C(S)OR  +  2 NaCl
  Xanthates bind to transition metal cations as bidentate ligands.  The charge-neutral complexes are soluble in organic solvents.
caption: Structure of typical metal tris(ethylxanthate) complex.[6]
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