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
edit- Thiosulfonates are organosulfur compounds with the formula RSO2S− and RSO2SR'
References
edit- ^ "IUPAC Gold Book - Bunte salts". doi:10.1351/goldbook.B00760.
{{cite journal}}: Cite journal requires|journal=(help) - ^ 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.
- ^ 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.
- ^ Distler, Harry "The Chemistry of Bunte Salts" Angewandte Chemie International Edition in English 1967, vol. 6, pp. 544-53. doi:10.1002/anie.196705441
- ^ 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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