Bunte salt

In organosulfur chemistry, a Bunte salt is an archaic name for salts with the formula RSSO3–Na+. They are also called S-alkylthiosulfates or S-arylthiosulfates.[1] These compounds are typically derived from alkylation on the pendant sulfur of sodium thiosulfate:[2]

RX + Na2S2O3 → Na[O3S2R] + NaX

They have been used as intermediates in the synthesis of thiols.[3] They are also used to generate unsymmetrical disulfides:

Na[O3S2R] + NaSR' → RSSR' + Na2SO3

According to X-ray crystallography, they adopt the expected structure with tetrahedral S(VI), an S-S single bond, and three S=O double bonds.[4]

See also
  • Thiosulfonates are organosulfur compounds with the formula RSO2S- and RSO2SR'

References
  1. "IUPAC Gold Book - Bunte salts".
  2. M. E. Alonso and H. Aragona (1978). "Sulfide Synthesis in Preparation of Unsymmetrical Dialkyl Disulfides: Sec-butyl Isopropyl Disulfide". Org. Synth. 58: 147. doi:10.15227/orgsyn.058.0147.CS1 maint: uses authors parameter (link)
  3. Distler, Harry "The Chemistry of Bunte Salts" Angewandte Chemie International Edition in English 1967, vol. 6, pp. 544-53. doi:10.1002/anie.196705441
  4. D.-Q. Sun, J.-K. Yang (2011). "(15-Crown-5-k-5O)[S-(E)-1,2-dichlorovinyl thiosulfato-[kappa]O]sodium". Acta Crystallographica E. 67 (7): m934. doi:10.1107/S1600536811022252. PMC 3151796. PMID 21836918.CS1 maint: uses authors parameter (link)
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