| 98% |
With phosphoric acid; sulfuric acid; dihydrogen peroxide In lithium hydroxide monohydrate; 1,2-dichloro-ethane at 70℃; for 1h; microwave irradiation; |
|
| 98% |
With lithium hydroxide monohydrate; fluorine; acetonitrile In dichloromethane; nitrogen Gas/liquid reaction; Continuous flow microreactor; |
|
| 97.2% |
With Cumene hydroperoxide In N,N-dimethyl-formamide at 90℃; for 12h; Flow reactor; |
|
| 95% |
With potassium peroxymonosulfate; C7F15C(O)CH3; Sodium hydrogenocarbonate In lithium hydroxide monohydrate at 25℃; |
|
| 94% |
With phosphoric acid disodium salt; dihydrogen peroxide; Hexafluoroacetone In 1,2-dichloro-ethane |
|
| 94% |
With methyltrioctylammonium tetrakis(diperoxotungsto)phosphate; dihydrogen peroxide In 1,2-dichloro-ethane at 70℃; for 1h; |
|
| 94% |
With 1,1,1,3',3',3'-hexafluoro-propanol; urea-hydrogen peroxide at 40℃; for 24h; |
|
| 94% |
With C30H24N2O7W; dihydrogen peroxide; Sodium hydrogenocarbonate In lithium hydroxide monohydrate; propan-2-one; acetonitrile at 30℃; for 2.5h; |
|
| 94% |
With Peroxyacetic acid; C26H30F6MnN8O8S2 In dichloromethane; acetonitrile at 0℃; for 0.55h; |
|
| 92% |
With potassium peroxomonosulfate; 1,1,1,3',3',3'-hexafluoro-propanol In lithium hydroxide monohydrate at 25℃; for 0.5h; |
|
| 91% |
With oxygen; manganese(III) triacetate; 2,2-dimethypropanal In various solvent(s) at 25℃; for 3h; |
|
| 91% |
With 3-chloro-benzenecarboperoxoic acid In dichloromethane other reagents: H2O2/KHCO3/dicyclohexylcarbodiimide, H2O2/Na3PO4*12H2O/dicyclohexylcarbodiimide, H2O2/Amberlite IRC-50/dicyclohexylcarbodiimide, H2O2/KHCO3/benzonitrile, H2O2/p-TsOH/dicyclohexylcarbodiimide, H2O2/HCl/DCC, H2O2/Amberlite IR-120/DCC; |
|
| 91% |
With Peroxyacetic acid; manganese(II) perchlorate; ammonium hydrogen carbonate In lithium hydroxide monohydrate; glacial acetic acid; acetonitrile at 20℃; for 0.666667h; |
|
| 90% |
With fluorine In dichloromethane at 0℃; for 0.0166667h; |
|
| 90% |
With dihydrogen peroxide; glacial acetic acid In lithium hydroxide monohydrate; acetonitrile at 4℃; for 0.0833333h; |
|
| 90% |
With 1,1,2,2-tetrahydroperoxy-1,2-diphenylethane; potassium hydroxide In acetonitrile at 20℃; for 2h; |
Epoxidation of alkenes (Scheme 2, entry 2) General procedure
General procedure: To a stirred solution of alkene (1 mmol) and THPDPE (1.5 mmol) in CH3CN (4 mL), KOH (1 M, 1 mL) was added and the mixture was stirred at room temperature for an appropriate time. After the completion of the reaction as monitored by TLC (hexane- Ethyl Acetate, 8:2) the mixture was quenched with Na2SO3 solution (3 M, 1 mL) and extracted with CH2Cl2 (3 × 5 mL). All of the products were characterized on the basis of their melting points, IR, 1H NMR, and 13C NMR spectral analysis and compared with those reported |
| 88% |
With 1,1,1,3',3',3'-hexafluoro-propanol; dihydrogen peroxide In lithium hydroxide monohydrate at 20℃; for 24h; |
|
| 88% |
With dihydrogen peroxide; tetraphenylphosphonium cation; Sodium hydrogenocarbonate In acetonitrile at 25℃; for 1.75h; |
|
| 87.2% |
With sodium wolframate; CH6NO3P; dihydrogen peroxide; methyl tri-n-octyl ammonium hydrogen sulfate at 90℃; for 2h; |
|
| 87% |
With Aminomethylphosphonic acid; dihydrogen peroxide In lithium hydroxide monohydrate at 90℃; for 2h; |
|
| 87% |
With C7H5MoNO8(2-)*2C24H20P(1+)*H2O; dihydrogen peroxide; Sodium hydrogenocarbonate In acetonitrile at 40℃; for 4h; Air; |
|
| 87% |
With 1-hexyl-3-methylimidazolium β-octamolybdate; dihydrogen peroxide In lithium hydroxide monohydrate; acetonitrile at 60℃; for 4h; Green chemistry; |
|
| 86% |
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at -40℃; for 6h; |
|
| 86% |
With potassium peroxomonosulfate; 2,2,2-trifluoro-1-(3-fluorophenyl)ethan-1-one; Sodium hydrogenocarbonate In lithium hydroxide monohydrate; acetonitrile at 20℃; for 12h; |
|
| 86% |
With Oxone; ammonium hydrogen carbonate In lithium hydroxide monohydrate; acetonitrile at 20℃; for 2h; |
|
| 86% |
With oxygen; 2-Methylpropanal In acetonitrile at 60℃; for 24h; |
|
| 86% |
Stage #1: 1-dodecene With trifluorormethanesulfonic acid; tetra-n-butylammonium tetrafluoroborate; N,N,N-tributyl-1-butanaminium iodide; dimethyl sulfoxide In dichloromethane at -78 - 0℃; for 1h; Inert atmosphere; Electrochemical reaction;
Stage #2: With sodium methoxide In methanol; dichloromethane at 25℃; for 0.0833333h; Inert atmosphere; Electrochemical reaction; |
Typical procedure for the generation of 1-I and the synthesis of epoxides
General procedure: In the anodic chamber were placed Bu4NI (91.7 mg, 0.248 mmol), Bu4NBF4 (102 mg, 0.3 mmol), DMSO(1 mL), and 0.3 M Bu4NBF4/CH2Cl2 (9 mL). In the cathodic chamber were placed TfOH (60 μL, 0.68 mmol)and 0.3 M Bu4NBF4/CH2Cl2 (10 mL). The constant current electrolysis (8.0 mA) was carried out at -78 °Cwith magnetic stirring until 2.1 F mol-1 of electricity was consumed. To the anodic chamber was added asolution of (Z)-5-decene (2a) (27.9 mg, 0.199 mmol) in CH2Cl2 (0.5 mL), and to the cathodic chamber 0.5mL of CH2Cl2 was added at -78 °C. The solution was stirred for 30 min at -78 °C then stirring wascontinued for 30 min at 0 °C. NaOMe (5.0 M in MeOH, 0.2 mL) was added to both the anodic and thecathodic chambers, and the resulting mixture was warmed to 25 °C and stirred for 5 min. The solution in theanodic chamber was filtered through a short column (2 x 4 cm) of silica gel to remove Bu4NBF4 by usingEt2O as an eluent. The GC analysis using hexadecane as an internal standard indicated that(5R*,6S*)-5,6-epoxydecane (6a) was obtained in 96% yield (0.191 mmol). |
| 85% |
With C9H6NO(1-)*C24H20P(1+)*MoO(4+)*2O2(2-); dihydrogen peroxide; Sodium hydrogenocarbonate In propan-2-one; acetonitrile at 25℃; for 2.5h; |
|
| 80% |
With WO3(3.5 wt%)-ZnO(0.8 wt%)/SnO2; dihydrogen peroxide; carbonic acid dimethyl ester In lithium hydroxide monohydrate at 59.84℃; for 4h; chemoselective reaction; |
|
| 79% |
With tert.-butylhydroperoxide In toluene at 79.84℃; for 5.83333h; |
|
| 79% |
With sodium (meta)periodate In lithium hydroxide monohydrate; acetonitrile at 20℃; for 0.25h; Sonication; |
General procedure for the epoxidation of alkeneswith sodium periodate in the presenceof [Ru(salophen)ClAp-MWCNT], [Ru(salophen)ClApy-MWCNT] and [Ru(salophen)ClDAB-MWCNT]catalysts.
General procedure: In a 25 mL round-bottom flask, a mixture of alkene (0.5 mmol) and catalyst (250 mg) in acetonitrile (5 mL) was prepared. Then, NaIO4 (220 mg, 1 mmol) was dissolved in H2O (5 mL) and added to the above mixture. The mixture was stirred with a magnetic stirrer at room temperature and atmospheric pressure. The progress of the reaction was monitored by gas chromatography (GC). At the reaction, the catalyst was filtered and the catalyst were recovered. |
| 77% |
With picoline; meso-tetrakis(2,6-dichlorophenyl)porphyrinatomanganese(III) acetate; magnesium monoperoxyphthalate hexahydrate In dichloromethane at 0℃; for 0.0666667h; |
|
| 77% |
With NHPI; oxygen; acetaldehyde In acetonitrile at 60℃; for 1h; Continuous flow reactor; |
|
| 75% |
With 3-chloro-benzenecarboperoxoic acid In dichloromethane |
|
| 75% |
With dihydrogen peroxide In lithium hydroxide monohydrate at 59.84℃; for 4h; Autoclave; |
|
| 74% |
With Isopropylbenzene at 105℃; for 24h; |
28 Example 28: Preparation of 1,2-epoxydodecane
N-dodecene (168.32 mg, 1.0 mmol) was added to a 50 mL reaction tube, and 3 mL of cumene was added; then, the reaction was performed in an air atmosphere at 105 ° C. After 24 hours, the reaction was complete. Then CH3NO2 was added as an internal standard for NMR analysis. The yield was 74%. |
| 72% |
With potassium carbonate; propan-2-one In lithium hydroxide monohydrate; benzene at 8 - 10℃; for 3h; |
|
| 72% |
With urea hydrogen peroxide; [1-heptyl-3-methylimidazolium][ReO4] at 70℃; for 6h; Ionic liquid; Green chemistry; |
2.4 Establishment of a catalytic system
General procedure: Generally, the oxidant H2O2 was used in the epoxidationof olefins, however, the presence of free hydrogen ions H? in the system caused the epoxycompound to ring-open to produce diol, which led tothe decrease of the selectivity of the reaction.42 Toincrease the yield and selectivity of the epoxidation ofolefins, the UHP was used as an oxidant, which had agood oxidation effect without producing diol, and theselectivity almost up to 100%.43To evaluate the catalytic effect of rhenium ionic liquid[Smim][ReO4] on epoxidation of olefin, the synthesizedionic liquid [Smim][ReO4] was selected as agreen solvent and catalyst, cyclohexene and cyclooctenewere used as reaction substrates, and the UHP wasselected as an oxidant in this paper for homogeneouscatalyzed epoxidation of olefin. The reaction productswere detected by gas chromatography (GC). |
| 71% |
With dirhodium(II) tetraacetate; oxygen; 3-methylbutyrylaldehyde In 1,2-dichloro-ethane at 20℃; for 27h; |
4.3 General procedure for epoxidation of alkenes in Table 1, entries 2, 9, and 10
General procedure: The round bottom flask was charged with Rh2(OAc)4 (4.4 mg, 0.01 mmol), and alkene (1.0 mmol) followed by addition of dichloroethane (3.0 mL). Then, isovaleraldehyde (433 mL, 4.0 mmol) was added in one portion. Flask was capped with septa and balloon with oxygen was attached. Completion of reaction was monitored by GC-MS. When done, solvent was removed on rotary evaporator and oily residue was purified by flash chromatography using ether-hexanes solvent mixtures. All epoxide product spectroscopic data were in agreement with literature data. |
| 70% |
With dihydrogen peroxide In 1,2-dichloro-ethane at 40℃; for 24h; |
|
| 70.8% |
With Mn(N,N'-dimethyl-N,N'-bis(2-pyridylmethyl)-1,2-ethanediamine)Cl<SUB>2</SUB>; [bis(acetoxy)iodo]benzene; scandium trifluoromethanesulphonate In dichloromethane; propan-2-one at -0.16℃; for 11.5h; |
|
| 68% |
With tert.-butylhydroperoxide; bis(acetylacetonato)dioxidomolybdenum(VI); N,N′-dimethylethylenediamine In Carbon tetrachloride; benzene at 70℃; for 1h; |
|
| 68.7% |
With {(N,N',N''-trimethyl-1,4,7-triazacyclononane)2Mn(IV)2(μ-O)3}(PF6)2*H2O; dihydrogen peroxide; scandium trifluoromethanesulphonate In lithium hydroxide monohydrate; acetonitrile at -0.16℃; for 2h; |
|
| 68% |
With tert.-butylhydroperoxide In lithium hydroxide monohydrate; acetonitrile at 82℃; for 12h; Sealed tube; |
5. Representative procedure for the epoxidation of alkenes
General procedure: The CoNPs/MgO catalyst was activated by heating in an oven at 150 °C for 1 h. To avigorously stirred suspension of the CoNPs/MgO catalyst (10 mg) in MeCN (1.0mL) under air the corresponding alkene (0.5 mmol in 1.0 mL MeCN) and TBHP (63 μL of an 80 wt % solution in H2O, 0.5 mmol in 1.0 mL MeCN) were added and thesealed reaction flask was immersed in an oil bath at the reflux temperature ofMeCN (82 °C). The reaction mixture was stirred at this temperature until nofurther conversion of the starting alkene was observed (TLC, GC). Then, the reactionmixture was centrifuged and the supernatant removed. The solvent was evaporated invacuo, and the crude product was purified by flash column chromatography (silicagel, hexane/AcOEt) to give the corresponding epoxide. The recovered solid catalystwas washed with acetonitrile (3 × 2 mL) and dried in oven (150 °C, 1 h) for its reuse. |
| 62% |
With oxygen; 2-oxocyclopentanecarboxylic acid methyl ester In acetonitrile at 25℃; for 25h; |
|
| 62% |
With oxygen; 2-Methylpropanal In acetonitrile Ambient temperature; |
|
| 62% |
With oxygen; 2-Methylpropanal In acetonitrile at 25℃; for 24h; |
|
| 62% |
With Co(II) complex with Schiff base from salicylaldehyde and L-serine methyl ester; oxygen; 2-oxocyclopentanecarboxylic acid methyl ester In acetonitrile at 25℃; for 25h; epoxidation of other alkenes; |
|
| 62% |
With tert.-butylhydroperoxide In lithium hydroxide monohydrate; acetonitrile at 50℃; for 4h; |
General procedure for the catalytic oxidation reaction
General procedure: In a typical experiment, a mixture of 2 mmol of tert-butyl hydroperoxide (TBHP, 70% aqueous solution) oxidizing agent and 1 mmol of alkene or alkane and 0.028 mmol (100 mg) of γ-Fe2O3[VO(salenac-OH)] in 5 mL of CH3CN was preparedin a test tube. A magnetic hotplate stirrer was used to stirring the reaction mixture at 50 °C, and the reaction progress was supervised using thin layer chromatography (TLC) or gas chromatography (GC). Having the reaction completed, 20 mL of CH2Cl2 was added to the reaction mixture to dilute it and an external magnet was used to remove the catalyst. Using CH2Cl2, the catalyst was completely washed and the combined washings were passed through a silica gel column to purify the product. |
| 61% |
With 2-hydroxypyridine; dihydrogen peroxide; diethyl dicarbonate In diethyl ether; dichloromethane for 3h; Ambient temperature; |
|
| 60% |
With manganese(II) p-aminobenzoate; oxygen; cobalt(II) p-aminobenzoate In N,N-dimethyl-formamide at 130℃; for 14h; |
|
| 59% |
Stage #1: 1-dodecene With NBS; dimethyl sulfoxide at 10℃; for 0.416667h; Inert atmosphere;
Stage #2: With 1,8-diazabicyclo[5.4.0]undec-7-ene In dimethyl sulfoxide at 10℃; for 0.5h; Inert atmosphere; |
|
| 58% |
With tert.-butylhydroperoxide In lithium hydroxide monohydrate; 1,2-dichloro-ethane at 50℃; for 4h; chemoselective reaction; |
General procedure for epoxidation of alkeneswith tert-BuOOH catalyzed by CoFe2O4SiO2[MoO2(salenac-OH)]
General procedure: 2 mmol of tert-BuOOH (TBHP, 70% aqueous solution) wereadded to a mixture of alkenes (1 mmol) and CoFe2O4SiO2[MoO2(salenac-OH)] (0.030 g) in 4 mL of 1,2-dichloroethanesolvent. The mixture thus obtained was stirred at50 °C under ambient pressure, and the reaction progress wasmonitored by gas chromatography (GC). Upon completingthe reaction, the catalyst was collected using an externalmagnet, rinsed using CH2Cl2,dried at 80 °C in an oven,and reused under the same reaction conditions. The productswere finally extracted with Et2Oand purified by columnchromatography using silica gel. |
| 58% |
With tert.-butylhydroperoxide In lithium hydroxide monohydrate; 1,2-dichloro-ethane at 50℃; for 4h; chemoselective reaction; |
General procedure for epoxidation of alkeneswith tert-BuOOH catalyzed by CoFe2O4SiO2[MoO2(salenac-OH)]
General procedure: 2 mmol of tert-BuOOH (TBHP, 70% aqueous solution) wereadded to a mixture of alkenes (1 mmol) and CoFe2O4SiO2[MoO2(salenac-OH)] (0.030 g) in 4 mL of 1,2-dichloroethanesolvent. The mixture thus obtained was stirred at50 °C under ambient pressure, and the reaction progress wasmonitored by gas chromatography (GC). Upon completingthe reaction, the catalyst was collected using an externalmagnet, rinsed using CH2Cl2,dried at 80 °C in an oven,and reused under the same reaction conditions. The productswere finally extracted with Et2Oand purified by columnchromatography using silica gel. |
| 56% |
With tert.-butylhydroperoxide In acetonitrile at 80℃; for 4.5h; |
2.3 General Procedure forEpoxidation ofOlefinswithtert-BuOOHCatalyzed byRunp-nSTDP
General procedure: The catalytic oxidation reactions of alkenes were carried outin a 25ml flask equipped with a magnetic stirrer and a refluxcondenser. In a typical run, the reaction vessel was chargedwith ruthenium catalyst (40mg, 0.84mol %), CH3CN(5ml), substrate (0.5mmol) and tert-BuOOH (1mmol).The reaction mixture was refluxed in an oil bath at 80°Cand its progress was monitored by GC. At the end of thereaction, the catalyst was removed by simple filtration andwashed with the adequate amount of acetonitrile (5ml) andH2O(5ml). Later on, the products were extracted with Et2Oand purified on a silica gel column (Et2O/n-hexane: 4:1).v |
| 53.1% |
With [(N-(2-pyridylmethyl)iminodiethanol)2Co3(CH3COO)4]; 3-chloro-benzenecarboperoxoic acid In dichloromethane; acetonitrile at 20℃; for 0.166667h; |
|
| 52% |
With Ni(N-(2-pyridylmethyl)-N’-(2-hydroxyethyl)ethylenediamine)(N3)2; 3-chloro-benzenecarboperoxoic acid In dichloromethane; acetonitrile at 20℃; for 0.166667h; |
|
| 50% |
With MoO5*(Et)3PO*MeOH for 72h; |
|
| 50% |
With iron(II) trifluoromethanesulfonate; 2-Picolinic acid; dihydrogen peroxide; N-methyl-N,N-bis(2-pyridylmethyl)amine In acetonitrile at 20℃; for 0.5h; |
|
| 48% |
With dihydrogen peroxide In benzene at 70℃; for 20h; |
|
| 45% |
With tert.-butylhydroperoxide In dichloromethane at 35℃; for 24h; |
|
| 45% |
With tert.-butylhydroperoxide In 2,2,4-trimethypentane; dichloromethane at 34.9℃; for 24h; |
|
| 45.1% |
With aluminium trifluoromethanesulphonate; Mn(tris(pyridin-2-ylmethyl)amine)Cl2; [bis(acetoxy)iodo]benzene In dichloromethane; acetonitrile at -0.16℃; for 3.5h; |
|
| 44.3% |
With [NiII(2-(di(pyridin-2-ylmethyl)amino)-N-(2-(5-methylpyridin-2-yl)phenyl)acetamidate)](ClO4); 3-chloro-benzenecarboperoxoic acid In acetonitrile at 25℃; for 0.166667h; |
|
| 42% |
With dihydrogen peroxide; tetra(n-hexyl)-ammonium chloride In benzene at 70℃; for 20h; |
|
| 38% |
With N,N′-bis(salicylidene)ethylenediaminocobalt(II); oxygen In acetonitrile at 20℃; for 20h; |
|
| 37% |
With oxygen; copper (II) acetate; 2-Methylpropanal In acetonitrile at 60℃; for 20h; |
|
| 35% |
With tetrahexylammonium chloride; dihydrogen peroxide In benzene at 75℃; for 20h; |
|
| 29% |
With dihydrogen peroxide In benzene at 70℃; for 20h; |
|
| 22.3% |
With C30H33Cl2MnN2O5; 3-chloro-benzenecarboperoxoic acid In dichloromethane; acetonitrile at 22℃; for 0.116667h; |
2.3 Alkene epoxidations by MCPBA with Mn(III) catalysts 1a-1c
General procedure: MCPBA (1×10-4 mol) was added to a mixture of the substrate (3.5×10-5 mol), Mn catalyst (1×10-3 mmol) and solvent (1.0mL, CH3CN/CH2Cl2=50:50), and the mixture was shaken at 22°C for 7min. Alkene oxidation and stilbene oxidation were analyzed by GC and HPLC, respectively. |
| 18% |
With tert.-butylhydroperoxide; [Mo2(O)4[2,2'-(1,3-phenylene)bis(4,5-dihydrooxazole-4,2-diyl)]dimethanol}(acac)2] In 1,2-dichloro-ethane for 10h; Reflux; |
2.3. General procedure for oxidation of alkenes with TBHP catalyzed by Mo BOX complex
General procedure: In a round-bottom flask (25 mL) equipped with a reflux condenser, a gas inlet and a magnetic stirrer, a solution of alkene (1 mmol) in 1,2-dichloroethane (4 mL) was prepared. The molybdenum BOX complex (8 mg, 0.01 mmol, 0.02 mmol Mo) and TBHP (2 mmol) was added to this solution and the reaction mixture was stirred under reflux conditions. The reaction progress was monitored by GC. After completion of the reaction, the mixture was directly passed through a short column of silica-gel (1:1,n-hexane-ethyl acetate) to remove the catalyst. The elute was evaporated under reduced pressure and the remaining residue was purified by silica-gel plate chromatography (eluted withCCl4:Et2O = 9:1) to afford the corresponding epoxide. |
| 17% |
With tetran-butylammonium salt of [γ-SiW10O34(H2O)2](4-); dihydrogen peroxide In lithium hydroxide monohydrate; ethyl acetate at 59.84℃; for 27h; |
|
| 87 % Chromat. |
With sodium wolframate; phosphoric acid; Aliquat; dihydrogen peroxide In 1,2-dichloro-ethane at 70℃; for 1h; pH 1.6; |
|
|
With lithium hydroxide monohydrate; fluorine In acetonitrile Yield given; |
|
|
With Peroxyacetic acid Ambient temperature; |
|
| 62.9 % Chromat. |
With oxygen In 1,2-dichloro-benzene at 110℃; for 7.7h; Further byproducts given. Yields of byproduct given; |
|
|
With benzoic acid sodium salt; dihydrogen peroxide In dichloromethane; lithium hydroxide monohydrate at 0℃; for 5h; |
|
| 79 % Chromat. |
With dihydrogen peroxide; n-tetradecanoic acid at 25℃; for 24h; immobilised Candida antarctica lipase (comp. A and B); |
|
|
With 4-tert-butylpyridine; sodium chlorine monoxide; (5,10,15,20-tetrakis(2,6-dichlorophenyl)porphyrinato)manganese(III) chloride; Sodium hydrogenocarbonate In dichloromethane; lithium hydroxide monohydrate at 10℃; for 20h; Yield given; |
|
| 99 % Chromat. |
With dihydrogen peroxide In benzene at 70℃; for 20h; |
|
| 92 % Chromat. |
With dihydrogen peroxide; benzoic acid In dichloromethane; lithium hydroxide monohydrate at 0℃; for 0.25h; |
|
|
With 3-chloro-benzenecarboperoxoic acid |
|
| 60 % Spectr. |
With bis(diphenylphosphinic) anhydride; dihydrogen peroxide; potassium carbonate In tetrahydrofuran at -5℃; for 48h; |
|
|
With Peroxyacetic acid In acetonitrile at 20℃; |
|
| 14 % Chromat. |
With sodium (meta)periodate In dichloromethane; lithium hydroxide monohydrate at 1.5℃; for 15h; |
|
| 37 % Chromat. |
With oxygen; 3-methylbutyrylaldehyde In various solvent(s) at 25℃; for 14h; |
|
|
With oxygen; 3-methylbutyrylaldehyde In acetonitrile at 25℃; for 14h; Yield given; |
|
| 67 % Chromat. |
With sodium chlorine monoxide; Mn(III)-5,10,15,20-tetrakis(2,6-dichlorophenyl)porphyrin; 1-n-Hexylimidazole In dichloromethane; lithium hydroxide monohydrate at 0℃; for 6h; |
|
|
With Peroxyacetic acid In acetonitrile at 20℃; other catalysts; |
|
| 37 % Chromat. |
With oxygen; 3-methylbutyrylaldehyde In various solvent(s) at 25℃; for 14h; other reagents; |
|
|
With Sal-Phe-Mn; oxygen at 100℃; for 12h; |
|
| 37.4 % Chromat. |
With oxygen; 2-Methylpropanal In 1,2-dichloro-ethane at 20℃; for 13h; |
|
|
With phenylarsonic acid; dihydrogen peroxide In various solvent(s) at 60℃; |
|
| 22 % Chromat. |
With sodium (meta)periodate In lithium hydroxide monohydrate; acetonitrile for 12h; |
|
|
With glutamic acid salicylaldehyde Shiff base cobalt; oxygen at 100℃; for 10h; |
|
|
With dihydrogen peroxide |
|
| 81 % Chromat. |
With oxygen; acetaldehyde In acetonitrile at 20℃; for 23h; |
|
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