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Bunte salt

From Wikipedia, the free encyclopedia
General chemical structure of a Bunte salt

Inorganosulfur chemistry, aBunte salt is an archaic name for salts with the formulaR−S−SO3Na+. They are also calledS-alkylthiosulfates orS-arylthiosulfates.[1] These compounds are typically derived fromalkylation on the pendantsulfur ofsodium thiosulfate:[2][3]

RX + Na2S2O3 → RS−SO3Na+ + NaX

They have been used as intermediates in the synthesis ofthiols.[4] They are also used to generateunsymmetrical disulfides:

RS−SO3Na+ + NaSR' → RS−SR' +Na2SO3

According toX-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

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References

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  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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