| 97% |
With dipyridinium dichromate In dichloromethane at 20℃; for 1h; Inert atmosphere; Molecular sieve; |
|
| 95% |
With 2,2,6,6-tetramethyl-piperidine-N-oxyl; [bis(acetoxy)iodo]benzene In dichloromethane for 2.5h; |
|
| 95% |
With oxygen; triethylamine In tetrahydrofuran; toluene at 45℃; for 20h; |
|
| 91% |
With benzophenone; (π-C5H5)2Zr{OC(CH3)2H}2 In toluene for 8h; Heating; |
|
| 91% |
With chlorine-triphenylphosphine; dimethyl sulfoxide; triethylamine In dichloromethane at -78 - 20℃; for 3.25h; |
|
| 90% |
In neat (no solvent) at 20℃; for 0.0666667h; Microwave irradiation; |
General procedure
General procedure: In a small-scale experiment 4-hydroxypyridinium chlorochromate functionalized silica gel (3.95 g, contain 10 mmol of 4-hydroxypyridinium chlorochromate) an alcohol (10 mmol) was rapidly added at room temperature and the resulting mixture stirred vigorously for the appropriate time. The mixture was irradiated for the time indicated in the table by microwave radiation (Table 2). The progresses of the reactions were monitored by TLC. After cooling to room temperature the product was extracted with diethyl ether (2 × 10 mL) and filtered. Evaporation of solvent gave a crude product which was passed through a short silica gel column by ethyl acetate: pet.ether (1:7) as eluent to afford the pure product. The structures of the products were confirmed by their melting point, IR and /or NMR spectral data and comparison with commercially available authentic samples.36-38 |
| 89% |
With potassium permanganate on Y-Zeolite In 1,2-dichloro-ethane for 6h; Ambient temperature; |
|
| 88% |
With 2,6-dicarboxypyridinium fluorochromate at 20℃; for 0.166667h; |
|
| 87% |
With tert.-butylhydroperoxide; tetrabutyl-ammonium chloride; 2,2′‐biquinoline‐4,4′‐dicarboxylic acid dipotassium salt In water at 20℃; for 24h; |
|
| 84% |
With pyridinium chlorochromate at 20℃; for 1.83333h; |
|
| 76% |
With Iron(III) nitrate nonahydrate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; oxygen; sodium chloride In 1,2-dichloro-ethane at 20℃; for 13h; |
|
| 72% |
With bromine; oxygen In acetic acid at 60℃; for 6h; |
|
| 71% |
With 2-chloro-1,3-dimethylimidazolinium chloride; dimethyl sulfoxide; triethylamine In dichloromethane at 20℃; for 72h; |
|
| 70% |
With 2,2,6,6-tetramethyl-piperidine-N-oxyl; [bis(acetoxy)iodo]benzene In dichloromethane at 19.85℃; for 2h; |
|
| 70% |
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene In dichloromethane at 20℃; for 2h; |
|
| 70% |
With titanium(IV) oxide; oxygen at 29.84℃; for 24h; Sealed tube; Irradiation; |
|
| 66% |
With octadecafluorodecahydronaphthalene (cis+trans); dihydrogen peroxide at 22℃; for 8h; |
|
| 64% |
With chromic acid In acetone at 0℃; |
|
| 61% |
With potassium permanganate; copper(II) sulfate In dichloromethane for 24h; Heating; |
|
| 48% |
With oxygen In dimethyl sulfoxide at 135℃; for 3h; |
|
| 35% |
With manganese(IV) oxide In tetrahydrofuran for 8h; Reflux; |
|
| 30% |
With allyl diethyl phosphate; potassium carbonate In N,N-dimethyl-formamide for 3.25h; |
|
| 11% |
With sodium permanganate In hexane at 69℃; for 24h; |
|
|
With manganese(IV) oxide In Petroleum ether |
|
|
With Py*HClCrO3 |
|
|
With dimethyl sulfoxide; triethylamine; trifluoroacetic anhydride |
|
|
With dipyridinium dichromate In dichloromethane |
|
| 92 % Chromat. |
With potassium permanganate; bentonite In dichloromethane for 60h; Heating; |
|
| 43.6 % Chromat. |
With potassium permanganate In benzene at 50℃; for 24h; Irradiation; |
|
|
With jones reagent In acetone at 5 - 10℃; |
|
| 54 % Turnov. |
With N-hydroxyphthalimide; cobalt(III) acetylacetonate; oxygen In acetonitrile at 75℃; for 5h; |
|
| 53 % Chromat. |
With palladium diacetate; oxygen In dimethyl sulfoxide at 80℃; for 24h; |
|
| 47 % Chromat. |
With manganese(IV) oxide; molecular sieve In hexane for 12h; Heating; |
|
|
With pyridinium chlorochromate |
|
| 80 % Chromat. |
With silica-supported 1-hydroxy-1,2-benziodoxol-3(1H)-one 1-oxide In tetrahydrofuran at 20℃; |
|
|
With [{nBu4N}5{PV2Mo10O40}]; dinitrogen monoxide In benzonitrile at 150℃; for 15h; |
|
|
With whole lyophilised cells of Rhodococcus ruber DSM 44541; acetone In phosphate buffer at 30℃; for 20h; |
|
|
With SiW11Zn; dihydrogen peroxide In water at 89.85℃; for 9h; |
|
|
Stage #1: 1-octen-3-ol With cis-[Ru(2,9-Me2phen)2(OH2)2](PF6)2 In acetonitrile at 55℃; for 0.5h;
Stage #2: With dihydrogen peroxide In acetonitrile for 12h; |
|
|
With oxygen at 79.85℃; for 3.5h; |
|
|
With oxygen at 120℃; for 3h; |
|
| 93 % Chromat. |
With oxygen; potassium carbonate In toluene at 80℃; for 6h; |
|
| 4.5 % Turnov. |
With oxygen In benzene-d6 at 60℃; for 24h; |
|
| 76 % Chromat. |
With oxygen; chloranil; decalin In water at 90℃; for 18h; |
|
| 67 % Chromat. |
With N-hydroxyphthalimide; oxygen; cobalt(II) acetate; 3-chlorobenzoate In ethyl acetate at 25℃; for 20h; |
|
| 2.6 % Chromat. |
With 1,4-dihydronicotinamide adenine dinucleotide; NAD In phosphate buffer at 30℃; for 72h; |
|
|
With air In toluene at 90℃; for 6h; |
|
|
With oxygen at 119.84℃; |
|
|
With oxygen In N,N-dimethyl-formamide at 139.84℃; for 1.3h; |
|
|
With oxygen; palladium diacetate; triethylamine In N,N-dimethyl acetamide at 70℃; for 4h; |
|
| 100 %Chromat. |
With oxygen; potassium carbonate In α,α,α-trifluorotoluene at 80℃; for 7h; |
|
|
Stage #1: 1-octen-3-ol With gold on titanium oxide In water at 90℃; for 0.166667h; Inert atmosphere;
Stage #2: With dihydrogen peroxide In water at 90℃; for 1.08333h; Inert atmosphere; chemoselective reaction; |
|
|
With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In ethyl acetate Reflux; |
|
| 90 %Chromat. |
With oxygen; potassium carbonate In α,α,α-trifluorotoluene at 95℃; for 5h; |
|
| 93 %Chromat. |
With Pd(0) nanoparticle supported on aminopropyl grafted silica-based mesocellular foam; air In para-xylene at 130℃; for 8h; |
|
|
With oxygen; palladium diacetate In N,N-dimethyl-formamide at 90℃; for 4h; Green chemistry; |
|
|
With Tween 20; crude enzyme extract from Marchantia polymorpha thalli In aq. phosphate buffer at 27℃; for 0.0833333h; Enzymatic reaction; |
4.6 Oxidoreductase assay
To estimate the oxidoreductase activity toward 5, crude enzyme soln. (100 μL) prepared as described in Section 4.4. was mixed with 10 mgmL-1 5 (10 μL) suspended in 0.2% Tween 20, and incubated at 27 °C for 5 min in 50 mM sodium phosphate (pH 7.0) with or without 5 mM NADH or NADPH. After the reaction, the C8 compounds were extracted with 1 mL of MTBE containing nonanyl acetate (1 μgmL-1), and quantitatively analyzed using GC-MS essentially as described in Section 4.4 but with the modified column condition [40 °C (5 min) to 200 °C (2 min) at 8 °Cmin-1 with He as a carrier gas at 26.7 cms-1]. |
| 34 %Chromat. |
With phosphomolybdic acid; oxygen; tetrabutylammonium acetate; palladium diacetate In ethyl acetate at 100℃; for 1h; |
|
|
With 6C16H36N(1+)*2Zn(2+)*4Na(1+)*[Bi2Zn2(ZnW9O34)2](14-); urea hydrogen peroxide adduct In acetonitrile at 70℃; for 3h; |
|
| 34 %Chromat. |
With manganese(II) triflate; 1-Adamantanecarboxylic acid; C32H38N4O2; dihydrogen peroxide In water; acetonitrile at 0℃; for 2h; chemoselective reaction; |
|
| 56 %Chromat. |
With oxygen In water at 80℃; for 8h; |
|
|
With gold; dihydrogen peroxide In methanol; water at 55℃; for 8h; Inert atmosphere; chemoselective reaction; |
Catalytic reaction
General procedure: The liquid-phase oxidation reactions were performed usinground bottom flask equipped with water condenser and a mag-netic stirrer. In a typical alcohol oxidation reaction, 0.67 g (5 mmol)of cinnamyl alcohol was mixed with 5 mL of methanol and 0.56 g(5 mmol) of dilute H2O2(30 wt% aqueous solution) in a 25 mL two-necked round bottom flask followed by addition of 5 wt% catalystwith respect to substrate. Cycloheptanone was used as an inter-nal standard to quantify the reaction product. The reaction wasperformed at 328 K while effectively circulation ice-cold waterthrough the condenser and the mixture was maintained under N2atmosphere using a N2balloon. The progress of the reaction wasmade by analyzing the products with a capillary gas chromato-graph (Agilent 13G, OV-1 column with flame ionization detector,FID). The quantification of products has been performed with spe-cial care using internal standard and response factor of reactantand products. For catalyst reusability study, the catalyst was recov-ered through centrifugation followed by activation under 5% H2(remaining N2) atmosphere at 180C. It is pertinent to mention thatlow-temperature activation was carried out to remove the physi-cally adsorbed organic reactant, product or solvent molecules fromthe metal surface of the used catalyst |
| 98 %Chromat. |
With dihydrogen peroxide In acetonitrile at 80℃; for 7.5h; |
|
|
With oxygen; palladium diacetate In toluene at 90℃; for 6h; Green chemistry; |
|
|
With [fac-N-(2-(diphenylphosphino)ethyl)-5,6,7,8-tetrahydroquinolin-8-amine]RuCl2(triphenylphosphine); potassium <i>tert</i>-butylate In para-xylene for 10h; Reflux; Inert atmosphere; |
|
|
With Dess-Martin periodane In dichloromethane at 20℃; |
|
|
With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In dimethyl sulfoxide at 20℃; for 2h; |
|
|
With Dess-Martin periodane In dichloromethane at 20℃; |
|
| > 99 %Chromat. |
With oxygen at 120℃; for 1h; |
|
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