Bunte salt

General chemical structure of a Bunte salt

In organosulfur chemistry, a Bunte salt is an archaic name for salts with the formula R−S−SO−3Na⁺. 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 → RS−SO−3Na⁺ + NaX

They have been used as intermediates in the synthesis of thiols. ^[4] They are also used to generate unsymmetrical disulfides:

RS−SO−3Na⁺ + NaSR' → RS−SR' + 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

• Thiosulfonates are organosulfur compounds with the formula RSO₂S⁻ and RSO₂SR'

References

1. "IUPAC Gold Book - Bunte salts" . IUPAC Gold Book . doi: 10.1351/goldbook.B00760 .
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.