FRINK Linked Data Fragments server

Matches in SemOpenAlex for { <https://semopenalex.org/work/W4247703558> ?p ?o ?g. }

• W4247703558 endingPage "10" @default.
• W4247703558 startingPage "1" @default.
• W4247703558 abstract "[74087-85-7] C3H6O2 (MW 74.09) InChI = 1S/C3H6O2/c1-3(2)4-5-3/h1-2H3 InChIKey = FFHWGQQFANVOHV-UHFFFAOYSA-N (selective, reactive oxidizing agent capable of epoxidation of alkenes and arenes,11 oxyfunctionalization of alkanes,19 and oxidation of alcohols,23 ethers,21 amines, imines,32 and sulfides35) Alternate Name: DDO. Physical Data: known only in the form of a dilute solution. Solubility: soluble in acetone and CH2Cl2; soluble in most other organic solvents, but reacts slowly with many of them. Form Supplied in: dilute solutions of the reagent in acetone are prepared from Oxone and acetone, as described below. Analysis of Reagent Purity: the concentrations of the reagent can be determined by classical iodometric titration or by reaction with an excess of an organosulfide and determination of the amount of sulfoxide formed by NMR or gas chromatography. Preparative Methods: the discovery of a convenient method for the preparation of dimethyldioxirane has stimulated important advances in oxidation technology.1 The observation2 that ketones enhance the decomposition of the monoperoxysulfate anion prompted mechanistic studies that implicated dioxiranes as intermediates.3 Ultimately, these investigations led to the isolation of dilute solutions of several dioxiranes.4 DDO is by far the most convenient of the dioxiranes to prepare and use (eq 1). Several experimental set-ups for the preparation of DDO have been described,4–6 but reproducible generation of high concentration solutions of DDO (ca 0.1M) is aided by a well-formulated protocol.6 The procedure involves the portionwise addition of solid Oxone (Potassium Monoperoxysulfate) to a vigorously stirred solution of NaHCO3 in a mixture of reagent grade Acetone and distilled water at 5–10 °C. The appearance of a yellow color signals the formation of DDO, at which point the cooling bath is removed and the DDO–acetone solution is distilled into a cooled (−78 °C) receiving flask under reduced pressure (80–100 Torr). After preliminary drying over reagent grade anhydrous MgSO4 in the cold, solutions of DDO are stored over molecular sieves in the freezer of a refrigerator at −10 to −20 °C. In instances where the concentration of DDO is crucial, analysis is typically based on reaction with an excess of an organosulfide monitored by NMR.4,7,8 (1) Concentrated solutions of DDO in chlorinated solvents may be obtained by a simple extraction technique. A fresh solution (50 mL) of isolated DDO (0.06–0.08 M in acetone), prepared as reported, is diluted with an equal volume of cold water (0–5 °C) and extracted in a chilled separatory funnel with four 10 mL portions of cold CH2Cl2, CHCl3, or CCl4 to yield a total volume of ca. 35 mL of extract (pale yellow DDO solution). In order to concentrate this DDO solution, the combined extracts in chlorinated solvent are washed three times in a separatory funnel at 0–5 °C with an equal volume of cold 0.01 M phosphate buffer (pH 7). The resulting solution is 0.19–0.36 M in DDO. Its concentration can be estimated by iodometry; the recovery of dioxirane from the initial acetone solution is 35–45% in most cases. 1H NMR spectroscopy analysis reveals that initial solvent acetone is not completely eliminated. Handling, Storage, and Precaution: solutions of the reagent can be kept in the freezer of a refrigerator (−10 to −20 °C) for as long as a week. The concentration of the reagent decreases relatively slowly, provided solutions are kept from light and traces of heavy metals. These dilute solutions are not known to decompose violently, but the usual precautions for handling peroxides should be applied, including the use of a shield. All reactions should be performed in a fume hood to avoid exposure to the volatile oxidant." @default.
• W4247703558 created "2022-05-12" @default.
• W4247703558 creator A5047518130 @default.
• W4247703558 creator A5047965283 @default.
• W4247703558 creator A5048574573 @default.
• W4247703558 creator A5050339551 @default.
• W4247703558 creator A5082424242 @default.
• W4247703558 creator A5082809165 @default.
• W4247703558 date "2021-02-03" @default.
• W4247703558 modified "2023-09-23" @default.
• W4247703558 title "Dimethyldioxirane (DDO)" @default.
• W4247703558 cites W1965903247 @default.
• W4247703558 cites W1966049780 @default.
• W4247703558 cites W1967615133 @default.
• W4247703558 cites W1968250801 @default.
• W4247703558 cites W1968391278 @default.
• W4247703558 cites W1972410449 @default.
• W4247703558 cites W1974492865 @default.
• W4247703558 cites W1975360738 @default.
• W4247703558 cites W1975543280 @default.
• W4247703558 cites W1975655962 @default.
• W4247703558 cites W1981181154 @default.
• W4247703558 cites W1985668085 @default.
• W4247703558 cites W1988226630 @default.
• W4247703558 cites W1989660900 @default.
• W4247703558 cites W1994173898 @default.
• W4247703558 cites W1996504774 @default.
• W4247703558 cites W1998352679 @default.
• W4247703558 cites W1998725697 @default.
• W4247703558 cites W2000776078 @default.
• W4247703558 cites W2003494876 @default.
• W4247703558 cites W2006784241 @default.
• W4247703558 cites W2008080056 @default.
• W4247703558 cites W2012057336 @default.
• W4247703558 cites W2012549562 @default.
• W4247703558 cites W2013160743 @default.
• W4247703558 cites W2013661001 @default.
• W4247703558 cites W2015637529 @default.
• W4247703558 cites W2017473308 @default.
• W4247703558 cites W2019084282 @default.
• W4247703558 cites W2019348035 @default.
• W4247703558 cites W2026226195 @default.
• W4247703558 cites W2028759057 @default.
• W4247703558 cites W2030469500 @default.
• W4247703558 cites W2030906679 @default.
• W4247703558 cites W2034050583 @default.
• W4247703558 cites W2034515987 @default.
• W4247703558 cites W2035386354 @default.
• W4247703558 cites W2036112546 @default.
• W4247703558 cites W2037285237 @default.
• W4247703558 cites W2038404922 @default.
• W4247703558 cites W2041536633 @default.
• W4247703558 cites W2043352235 @default.
• W4247703558 cites W2045052388 @default.
• W4247703558 cites W2050020731 @default.
• W4247703558 cites W2053122551 @default.
• W4247703558 cites W2055836983 @default.
• W4247703558 cites W2057181998 @default.
• W4247703558 cites W2059169016 @default.
• W4247703558 cites W2062705121 @default.
• W4247703558 cites W2063366716 @default.
• W4247703558 cites W2063537845 @default.
• W4247703558 cites W2064046071 @default.
• W4247703558 cites W2068756520 @default.
• W4247703558 cites W2070524210 @default.
• W4247703558 cites W2073270317 @default.
• W4247703558 cites W2074198668 @default.
• W4247703558 cites W2075334646 @default.
• W4247703558 cites W2075649369 @default.
• W4247703558 cites W2076777879 @default.
• W4247703558 cites W2083456096 @default.
• W4247703558 cites W2091388781 @default.
• W4247703558 cites W2092628009 @default.
• W4247703558 cites W2094678705 @default.
• W4247703558 cites W2099266073 @default.
• W4247703558 cites W2112758391 @default.
• W4247703558 cites W2116302310 @default.
• W4247703558 cites W2129840328 @default.
• W4247703558 cites W2136822274 @default.
• W4247703558 cites W2139494162 @default.
• W4247703558 cites W2148687615 @default.
• W4247703558 cites W2160185370 @default.
• W4247703558 cites W2294312508 @default.
• W4247703558 cites W2319137370 @default.
• W4247703558 cites W2416955878 @default.
• W4247703558 cites W2528592153 @default.
• W4247703558 cites W2782605873 @default.
• W4247703558 cites W2949074175 @default.
• W4247703558 cites W2949369035 @default.
• W4247703558 cites W2950225484 @default.
• W4247703558 cites W2950635137 @default.
• W4247703558 cites W2950688753 @default.
• W4247703558 cites W2951036260 @default.
• W4247703558 cites W2951361944 @default.
• W4247703558 cites W2951585956 @default.
• W4247703558 cites W2951877467 @default.
• W4247703558 cites W2951898370 @default.
• W4247703558 cites W2951963994 @default.

• next