General chemical structure of a 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][3]

RX + Na2S2O3 → Na[O3S2R] + NaX

They have been used as intermediates in the synthesis of thiols.[4] 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 sulfur(VI) atom, a sulfur-sulfur single bond, and three equivalent sulfur-oxygen bonds.[5]

See also

References

  1. ^ "IUPAC Gold Book - Bunte salts". doi:10.1351/goldbook.B00760. ((cite journal)): Cite journal requires |journal= (help)
  2. ^ M. E. Alonso; 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.
  3. ^ Reeves, J.T.; Camara, K.; Han, Z.S.; Xu, Y.; Lee, H.; Busacca, C.A.; Senanayake, C.H. (2014). "The Reaction of Grignard Reagents with Bunte Salts: A Thiol-Free Synthesis of Sulfides". Organic Letters. 16 (4): 1196–1199. doi:10.1021/ol500067f. PMID 24512478.
  4. ^ Distler, Harry "The Chemistry of Bunte Salts" Angewandte Chemie International Edition in English 1967, vol. 6, pp. 544-53. doi:10.1002/anie.196705441
  5. ^ 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.


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