SULFINIC ACIDS AND RELATED COMPOUNDS. 15. CONVENIENT METHODS FOR ESTERIFYING SENSITIVE SULFINIC ACID SALTS 1
- 1 November 1985
- journal article
- research article
- Published by Taylor & Francis in Phosphorus and Sulfur and the Related Elements
- Vol. 25 (2) , 161-165
- https://doi.org/10.1080/03086648508072729
Abstract
In a study of conversions of sensitive sulfinate salts to esters, a trisulfide bissulfinate, [NaO2S(CH2)4S]2S (1), was esterified with trialkyloxonium fluorborates. This procedure (Method A) was better for ethylation than use of ROH-HC1/BF3 (C2H5)2O (Method B). but Method B was better for methylation. Disodium 3-sulfinopropanoate (7) was best dimethylated with CH3OH/BF3 · (C2H5)2O without HCl (Method C). Method B or C gave satisfactory results with sodium p-toluenesulfinate (3), but ROH/BF3 · (C2H5)2O with the free acid was better than either (Method D). p-Tolylsulfonyldiazomethane did not esterify p-toluenesulfinic acid: only the sulfonate was isolated (10, 15–20% yield).Keywords
This publication has 19 references indexed in Scilit:
- Sulfinic acids and related compounds. 14. Derivatives of 3-sulfinopropanoic acidThe Journal of Organic Chemistry, 1983
- Sulfinic acids and related compounds. 13. Unsymmetrical disulfides based on methyl 4-mercaptobutanesulfinate and 4(S)- or 4(R)-mercaptoprolinesThe Journal of Organic Chemistry, 1981
- Organic disulfides and related substances. 38. Disulfide and trisulfide sulfinate salts as antiradiation drugsJournal of Medicinal Chemistry, 1975
- Organic disulfides and related substances. 36. Oxodisulfide cleavage reactions to form disulfides and trisulfidesThe Journal of Organic Chemistry, 1972
- Organic disulfides and related substances. 35. Preparation of unsymmetrical disulfides containing carboxylate moieties and neighboring-group effects of sulfinate and carboxylate moieties on disproportionationThe Journal of Organic Chemistry, 1972
- Organic disulfides and related substances. 33. Sodium 4-(2-acetamidoethyldithio)butanesulfinate and related compounds as antiradiation drugsJournal of Medicinal Chemistry, 1972
- Biologically oriented organic sulfur chemistry. 9. Carbonyl and thiocarbamoyl disulfides as inhibitory agents for Histoplasma capsulatumJournal of Medicinal Chemistry, 1971
- Organic disulfides and related substances. XXVII. Reactions and synthetic utility of cyclic disulfides, dioxides, and tetroxidesThe Journal of Organic Chemistry, 1969
- Organic Sulfur Compounds. VI. The Reactions of Arylsulfinic Acids with Alkyl ChlorocarbonatesBulletin of the Chemical Society of Japan, 1966
- CCCLIV.—Investigations on the dependence of rotatory power on chemical constitution. Part XXVII. The optical properties of n-alkyl p-toluenesulphinatesJournal of the Chemical Society, Transactions, 1925