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[ CAS No. 696-71-9 ]

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2D
Chemical Structure| 696-71-9
Chemical Structure| 696-71-9
Structure of 696-71-9 *Storage: {[proInfo.prStorage]}

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Product Details of [ 696-71-9 ]

CAS No. :696-71-9MDL No. :MFCD00001744
Formula : C8H16O Boiling Point : -
Linear Structure Formula :-InChI Key :N/A
M.W :128.21Pubchem ID :-
Synonyms :

Computed Properties of [ 696-71-9 ]

TPSA : - H-Bond Acceptor Count : -
XLogP3 : - H-Bond Donor Count : -
SP3 : - Rotatable Bond Count : -

Safety of [ 696-71-9 ]

Signal Word:WarningClass:
Precautionary Statements:P501-P270-P210-P264-P280-P370+P378-P301+P312-P330-P403+P235UN#:
Hazard Statements:H302-H227Packing Group:
GHS Pictogram:

Application In Synthesis of [ 696-71-9 ]

  • Downstream synthetic route of [ 696-71-9 ]

[ 696-71-9 ] Synthesis Path-Downstream   1~7

  • 1
  • [ 696-71-9 ]
  • [ 502-49-8 ]
YieldReaction ConditionsOperation in experiment
100% With dihydrogen peroxide; tetrabutylammonium hydrogensulfate In <i>tert</i>-butyl alcohol at 90℃; for 0.5h;
100% With ruthenium (III) chloride; iodobenzene; oxone In lithium hydroxide monohydrate; acetonitrile at 20℃; for 0.5h;
100% With ruthenium (III) chloride; iodobenzene; oxone In lithium hydroxide monohydrate; acetonitrile at 20℃; for 0.5h; Inert atmosphere;
100% With Ni(NTf2)2·xH2O; 4-mercapto-4-oxide-dinaphtho<2,1-d:1',2'-f><1,3,2>dioxaphosphepin; 9-mesityl-10-methylacridin-10-ium perchlorate In dichloromethane at 27 - 29℃; for 20h; Inert atmosphere; Irradiation;
100% With oxygen; sodium hydroxide In lithium hydroxide monohydrate at 90℃; for 12h;
99% With dihydrogen peroxide In benzene at 70℃; for 3h;
99% With air; potassium carbonate at 20℃; for 10h;
99% With Cu nanoparticles dispersed on La2O2CO3 In 1,3,5-trimethyl-benzene at 109.84℃; for 1h; Inert atmosphere;
99% With oxygen; potassium carbonate; 1,3-dibromo-1,3,5-triazinane-2,4,6-trione In lithium hydroxide monohydrate at 0℃; for 1h; Darkness; Green chemistry;
99% With aluminum(III) oxide In N,N-dimethyl-formamide at 120℃; for 6h; Inert atmosphere;
98% With mesoporous silica; copper(II) nitrate In Carbon tetrachloride for 1.5h; Zn(NO3)2, 2 h;
98% With Peroxyacetic acid In Carbon tetrachloride; dichloromethane at 0℃; for 0.5h;
98% With tetrabutylammonium bromide In benzotrifluoride at 20℃; for 5h; Inert atmosphere;
97% With oxygen In lithium hydroxide monohydrate at 25℃; for 2h;
96.1% With oxygen In lithium hydroxide monohydrate at 80℃; for 24h;
95% With nickel In benzene for 1.5h; Heating;
95% With oxygen; acetaldehyde In ethyl acetate at 20℃; for 1.5h;
95% With oxygen; acetaldehyde Ambient temperature;
95% With potassium peroxomonosulfate; (o-C6H4-CO2CH2)2CO; (ethylenedinitrilo)tetraacetic acid disodium salt; Sodium hydrogenocarbonate In acetonitrile for 4h; Ambient temperature;
95% With dihydrogen peroxide at 75℃; for 7h;
94% With tetrahexylammonium chloride; dihydrogen peroxide In benzene at 75℃; for 3h;
94% With NaNO2 In trifluoroacetic acid at 0 - 20℃; for 5h;
94% With aluminium(III) chloride; 1-decyl-4-aza-1-azoniabicyclo[2.2.2]octane chlorochromate In acetonitrile for 2.2h; Heating;
93% With chromium(VI) oxide; aluminum(III) oxide In hexane at 39.9℃; for 15h;
93% With oxygen In lithium hydroxide monohydrate at 60℃; for 60h;
93% With oxygen In lithium hydroxide monohydrate at 60℃; for 12h;
93% With oxygen In lithium hydroxide monohydrate at 60℃; for 60h; 4; 5 EXAMPLE 4In an ambient pressure oxygen atmosphere, 26.4 mg of cyclooctanol and 34.1 mg of the platinum catalyst obtained in Example 1 were agitated for twelve hours at 60° C. in 2 ml of water. The reaction mixture was subsequently extracted using ethyl acetate, and the organic layer was dried using magnesium sulfate, filtered and concentrated to obtain 22.6 mg (87% yield) of cyclooctanone. The reaction equation and the analytical results of the product are shown below.1H-NMR (400 MHz, solvent:CDCl3) δ: 1.25 (t, 2H, J=11.8 Hz), 1.33-1.40 (m, 4H), 1.50-1.57 (m, 4H), 1.84-1.90 (m, 4H), 2.40 (t, 4H, J=6.2 Hz); MS (m/z) 42, 55, 69, 83, 98, 111, 126 (M+); EXAMPLE 5In an ambient pressure oxygen atmosphere, 25 mg of cyclooctanol and 137 mg of the platinum catalyst obtained in Example 1 were agitated for sixty hours at 60° C. in 2 ml of water. The reaction mixture was subsequently extracted using ethyl acetate, and the organic layer was dried using magnesium sulfate, filtered and concentrated to obtain 22.8 mg (93% yield) of cyclooctanone.
93% With alcohol dehydrogenase (evocatal ADH 200); C44H28ClFeN4O12S4 at 20℃; for 24h; aq. phosphate buffer; Enzymatic reaction;
92% With NaBrO3 In chloroform; lithium hydroxide monohydrate for 3.1h;
92% With 1-butyl-3-methyl-1H-imidazol-3-ium bromide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione at 25℃; for 6h;
92% With trans-3,5-dihydroperoxy-3,5-dimethyl-1,2-dioxolane In acetonitrile at 20℃; for 0.5h;
92% With manganese(II) nitrate; C70H128N16O4; oxygen; cobalt(II) nitrate In glacial acetic acid at 40℃; for 2h;
92% With tert.-butylhydroperoxide In lithium hydroxide monohydrate; acetonitrile at 80℃;
92% With double-atom catalyst FeCo-DAC In n-octane at 160℃; for 48h; Inert atmosphere; Sealed tube;
91% With pyridinium chlorochromate at 20℃; for 1.33333h;
91% With iodine; bis(pyridine)iodonium(I) tetrafluoroborate; Cs2CO3 In acetonitrile at 60℃; for 3h;
91% With NaBrO3; 1-butyl-3-methyl-1H-imidazol-3-ium bromide at 70℃; for 150h;
90% With 6-((cobalt(II) 4,9,16,23-tetraaminephthalocyanin-4-yl))cellulose; oxygen; potassium hydroxide In o-dimethylbenzene at 20℃; for 10h; Green chemistry; Typical procedure for the oxidation of 1-phenyl-ethanol General procedure: 1-Phenyl-ethanol (0.14 g, 1.00 mmol) was added to a two-necked flask equipped with a gas bubbling tube containing colloidal of CoPcCell (0.05 g) and KOH (0.25 mmol) in o-xylene (5 mL) at room temperature. The mixture was stirred at room temperature under O2 atmosphere provided with a balloon. The progress of the reaction was followed by thin layer chromatography (TLC). Upon completion, CoPcCell was separated by filtration and washed with acetone (5 mL). Acetophenone was isolated from the mixture using column chromatography with n-hexane in 90% yield.
90% With potassium carbonate In lithium hydroxide monohydrate; dimethyl sulfoxide at 60℃; for 0.833333h;
89% With 4-methoxy-1-oxo-2,2,6,6-tetramethylpiperidinium chloride In dichloromethane for 1h; Ambient temperature;
89% With dihydrogen peroxide; 1-n-butyl-3-methylimidazolium tetrafluoroborate for 2h; Heating;
89% With potassium carbonate at 20℃; for 10h; Neat (no solvent);
88% With oxygen In lithium hydroxide monohydrate for 20h; Heating;
88% With oxygen In lithium hydroxide monohydrate for 20h; Heating;
88.8% With oxygen In lithium hydroxide monohydrate at 80℃; for 24h;
88% With tert.-butylhydroperoxide; [Re(p-NTol)Cl(2-(2-hydroxyphenyl)benzothiazole)(PPh3)2]·PF6; oxygen In lithium hydroxide monohydrate; acetonitrile at 70℃; for 14h;
87% With C26H16N6O4Ru; dihydrogen peroxide at 60℃; for 1h; General procedure: The catalytic oxidation of alcohol was carried out in a magnetically stirredglass reaction tube fitted with a reflux condenser. A typical procedure was asfollows using benzyl alcohol as model substrate: benzyl alcohol (2 mmol) andRu(bbp)(pydic) (2 103 mmol, 0.1 mol % based substrate) were added into areaction tube. The reactor containing this mixture was heated to 60 C in an oilbath under vigorous stirring, and then 30% H2O2 (10 mmol) was slowlydropped in. The resulting system was stirred at 60 C for 60 min. At the end ofreaction, the resulting products and unreacted substrate were extracted bydichloromethane three times. The extracted liquid mixture was analyzed byGC and GC-MS. GC analyses were performed on a Shimadzu GC-2010 pluschromatography equipped with Rtx-5 capillary column(30 m 0.25 mm 0.25 lm). GC-MS analyses were recorded on a ShimadzuGCMS-QP2010 equipped with Rxi-5 ms capillary column(30 m 0.25 mm 0.25 lm).
86% With {(N,N',N''-trimethyl-1,4,7-triazacyclononane)2Mn(IV)2(μ-O)3}(PF6)2*H2O; dihydrogen peroxide; trichloroacetic acid In lithium hydroxide monohydrate; acetonitrile at 20℃; for 16h;
85% With NaBrO3; phosphoric acid monosodium salt; iron(III) chloride In lithium hydroxide monohydrate; acetonitrile at 25℃; for 4h;
85% With 2,2,6,6-tetramethyl-1-piperidinyloxy free radical; dimethylsulfane; oxygen In chlorobenzene at 90℃;
85% With aluminium(III) chloride; 1-butyl-4-aza-1-azoniabicyclo[2.2.2]octane chlorochromate In acetonitrile for 4.5h; Heating;
85% With boron trifluoride diethyl ether complex In dichloromethane for 12h;
85% Stage #1: cyclooctanol With copper(II) bromide In acetonitrile at 20℃; for 0.05h; Inert atmosphere; Stage #2: With N,N'-di-tert-butyldiaziridin-3-one In acetonitrile at 20℃; for 12h;
84% With Dess-Martin periodane; glacial acetic acid In dichloromethane at 25℃; for 1h;
84% With tert.-butylhydroperoxide; dioxochromium(VI) bis(salicylaldehyde)ethylene diamine In benzene at 80℃; for 6h;
84% In para-xylene for 24h; Inert atmosphere; Reflux;
83% With molecular sieve; <PPh4><RuO2(OCOMe)Cl2> In dichloromethane for 1h; Ambient temperature;
83% With NaBrO3; ammonia hydrochloride In acetonitrile at 80℃; for 3h;
83% With manganese(III) tris(acetylacetonate); acetonitrile In Carbon tetrachloride at 200℃; for 3h;
83% With potassium peroxymonosulfate; C18H17IN2O7PolS(1-)*Na(1+); tetrabutylammonium hydrogensulfate In acetonitrile at 70℃; for 18h; Sealed tube; Green chemistry;
83% With cerium(III) bromide; dihydrogen peroxide In 1,4-dioxane; lithium hydroxide monohydrate at 20℃;
81% With sodium chlorine monoxide; Sodium hydrogenocarbonate; potassium bromide In dichloromethane at 20℃; for 0.25h;
81% With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; copper (II) acetate In lithium hydroxide monohydrate; acetonitrile at 20℃; for 8h; Green chemistry; General procedure: A mixture of alcohol (5.0 mmol), Cu(OAc)2 (9.1 mg, 0.05 mmol), and TEMPO (7.8 mg, 0.05 mmol) in CH3CN/H2O (5/10 mL) was stirred at room temperature for specified time. After completion of the reaction (monitored by TLC, eluents: petroleum ether/ethyl acetate = 4/1), dichloromethane (10 mL) was added to the resulting mixture. The dichloromethane phase was separated, and the aqueous phase was further extracted with dichloromethane (10 mL × 2). The combined organic layers were dried over anhydrous sodium sulfate and concentrated to give a residue, which was purified by column chromatography (eluents: petroleum ether/ethyl acetate = 10/1) to provide the desired product.
80% With dihydrogen peroxide at 70℃; for 3h;
80.1% With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; polymer-bound {NMe3(1+)*Br(OAc)2(1-)} In dichloromethane at 40℃; for 24h;
80% With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; bisacetoxybromate(I) resin In dichloromethane at 20℃; for 24h;
80% With [Cp*Ir(6,6'-dihydroxy-2,2'-bipyridine)(H2O)](OTf)2 In lithium hydroxide monohydrate for 20h; Inert atmosphere; Reflux;
79% With isocyanate de chlorosulfonyle; dimethyl sulfoxide; triethylamine In dichloromethane 1.) -78 deg C, 1.5 h, 2.) room temperature, 0.5 h;
79% With C17H16Cl2N3O2RuS; N-Methylmorpholine N-oxide In dichloromethane for 3h; Reflux;
78% With sodium chlorine monoxide In dichloromethane; lithium hydroxide monohydrate at 0℃; for 0.5h;
78% With [bis(acetoxy)iodo]benzene; fluorous-tagged TEMPO radical In dichloromethane at 20℃; for 14h;
78% With 2-Picolinic acid; Mn(ClO<SUB>4</SUB>)<SUB>2</SUB>.6H<SUB>2</SUB>O; dihydrogen peroxide; anhydrous Sodium acetate In acetonitrile at 0 - 20℃;
76% With anhydrous sodium carbonate; propan-2-one; 2,2'-biquinoline-4,4'-dicarboxylic acid dipotassium salt In lithium hydroxide monohydrate at 90℃; for 4h;
76% With anhydrous sodium carbonate; propan-2-one; 2,2'-biquinoline-4,4'-dicarboxylic acid dipotassium salt In lithium hydroxide monohydrate at 90℃; for 4h;
75% With HMTAB; mesoporous silica In lithium hydroxide monohydrate at 20℃; for 0.25h;
75% With C16H12Cl2N2O3RuS; N-Methylmorpholine N-oxide In dichloromethane at 4℃; for 1h; Molecular sieve; Reflux; General procedure: A solution of complex 1 (0.01mmol) in CH2Cl2 (25mL) was added to the mixture containing PhCH2OH (1mmol), NMO (3mmol) and molecular sieves. The reaction mixture was refluxed and conversion of PhCH2OH to PhCHO was monitored taking the reaction mixture at 10min time interval. The solvent of the reaction mixture was evaporated under reduced pressure. The residue was then extracted with diethyl ether, concentrated to ≈1mL. Conversions were determined by GC instrument equipped with a flame ionization detector (FID) using a HP-5 column of 30m length, 0.53mm diameter and 5.00μm film thickness. The column, injector and detector temperatures were 200, 250 and 250°C respectively. The carrier gas was N2 (UHP grade) at a flow rate of 30mL/min. The injection volume of sample was 2μL. The oxidation products were identified by GC co-injection with authentic samples. No significant conversion was observed after 50min. All other alcohols were oxidized by refluxing the reaction mixture for 1h and conversions were monitored following the identical protocol.
75% With nickel trifluoromethanesulfonate; cyclohexanone; 1,2-bis-(dicyclohexylphosphino)ethane In toluene at 110℃; for 12h; Schlenk technique;
74% With quinolinium fluorochromate In hexane for 6.5h; Heating;
72% With polymer-immobilized TEMPO radical; Sodium hydrogenocarbonate; sodium bromide In lithium hydroxide monohydrate at 0℃; Electrochemical reaction;
72% With dihydrogen peroxide; tungstic acid; 1-octyl-3-methylimidazolium bis(trifluoromethanesulfonyl)imide In lithium hydroxide monohydrate at 90℃; for 1h; Green chemistry; Optimized cyclohexanol oxidation with Aliquat 336 General procedure: Cyclohexanol (1.04 mL, 10 mmol, 1 equiv.), tungstic acid(58.9 mg, 0.24 mmol, 2.4 mol%), Aliquat 336 (275 mg, 0.68 mmol,6.8 mol%) and 30% hydrogen peroxide (2.04 mL, 20 mmol, 2 equiv.)were introduced into a glass tube. The mixture was stirred at90 C for 30 min. Then, the organic phase was extracted withethyl acetate (3×2 mL) and cyclohexane (2×2 mL). The combinedorganic phases were dried with MgSO4 and analysed bygas chromatography (GC). The same procedure was used from theother substrates: cyclopentanol (0.91 mL, 10 mmol, 1 equiv.), cycloheptanol(1.20 mL, 10 mmol, 1 equiv.) and cyclooctanol (1.32 mL,10 mmol, 1 equiv.).
72% With 1H-imidazole; tert.-butylhydroperoxide; [(R,R)-N,N’-bis(3,5-di-chlorosalicylidene)-1,2-cyclohexanediaminato](acetato) manganese(III) In acetonitrile at 20℃; for 12h; 5.1.7 Catalytic runs General procedure: The Mn catalyst (0.25% mol) and imidazol were added to 1.0mL of CH3CN, under stirring. After 10min, the substrate (1.0mmol) and TBHP (4.0mmol, in 2.0mL CH3CN) were added to the reaction flask. After 12h stirring at room temperature, the reaction mixture was filtered and analyzed by GLC using anisole as internal standard.
71% With C77H60Cl2N4O4PRu2; N-Methylmorpholine N-oxide In dichloromethane for 8h; Reflux;
71% Stage #1: cyclooctanol With NiCl2·6H2O; cadmium sulphide In acetonitrile for 0.00277778h; Schlenk technique; Sonication; Inert atmosphere; Stage #2: In acetonitrile at 20℃; for 48h; Irradiation; Inert atmosphere; Schlenk technique;
70% With pyridine; 1,4-diaza-bicyclo[2.2.2]octane; tetraethylammonium trichloride In acetonitrile Ambient temperature;
70% With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In 1-methyl-pyrrolidin-2-one at 20℃; for 2h;
70.9% With tert.-butylhydroperoxide; C48H45Cu4N16O14; potassium carbonate In lithium hydroxide monohydrate at 80℃; for 4h; Microwave irradiation;
69% With 4-iodyl-9-phenylacridine In chlorobenzene at 20℃; for 13h; Irradiation;
68% With acrylic acid methyl ester In lithium hydroxide monohydrate; N,N-dimethyl-formamide at 140℃; for 0.25h; microwave irradiation;
68% With 1H-imidazole; sodium (meta)periodate In lithium hydroxide monohydrate; acetonitrile at 20℃; for 2h;
67% With ammonium cerium (IV) nitrate; C15H26F6FeN4O6S2; lithium hydroxide monohydrate In acetonitrile at 0℃;
66% With C26H30F6MnN6O6S2; dihydrogen peroxide; glacial acetic acid In acetonitrile at 20℃; for 1h; chemoselective reaction;
65% With (p-cymene)Ru(μ-Cl)3RuCl(C2H4)(1,3-dimesitylimidazol-2-ylidene); Nitrous oxide In 1,2-dichloro-benzene at 150℃; for 18h;
64% With tert.-butylhydroperoxide; cis-(Cl,Cl)-[Re(p-NC6H4CH3)Cl2(indazole-3-carboxylate)(P(phenyl)3)] methanol solvate In lithium hydroxide monohydrate; acetonitrile for 11h;
62% With aluminum(III) oxide; quinolinium fluorochromate In hexane for 6h; Ambient temperature;
59% With 1H-imidazole; tert.-butylhydroperoxide; [(N,N′-bis(3,5-di-chloro-salicylidene)-2,3-diiminopyridine)(acetato)]manganese(III) In acetonitrile at 55℃; for 12h;
58.6% With lithium hydroxide monohydrate; [bis(trifluoroacetoxy)iodo]perfluorooctane; potassium bromide at 20℃;
58% With pyridine; iso-butyl hydroperoxide; C24H26FeN6(2+)*2CF3O3S(1-) In lithium hydroxide monohydrate; acetonitrile at 20℃; for 5h; Inert atmosphere;
48% With dihydrogen peroxide In benzene at 70℃; for 3h;
47.6% With tert.-butylhydroperoxide; OCu4(N(CH2CH2O)3)4(BOH)4(2+)*2BF4(1-)=[OCu4(N(CH2CH2O)3)4(BOH)4][BF4]2 In lithium hydroxide monohydrate; acetonitrile at 70℃; for 3h;
40% With potassium permanganate In acetonitrile at 5 - 20℃;

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  • 2
  • [ 696-71-9 ]
  • [ 499-44-5 ]
  • [ 93700-84-6 ]
  • 3
  • [ 696-71-9 ]
  • [ 284-20-8 ]
  • [ 502-49-8 ]
  • [ 21573-31-9 ]
  • [ 772-60-1 ]
YieldReaction ConditionsOperation in experiment
1: 8 % Turnov. 2: 31 % Turnov. 3: 46 % Turnov. With lead(IV) acetate; copper diacetate In benzene at 80℃; for 3.5h;
  • 4
  • [ 292-64-8 ]
  • [ 502-49-8 ]
  • [ 696-71-9 ]
YieldReaction ConditionsOperation in experiment
1: 80% 2: 19% With CoO40W12(5-)*3C30H24CoN6*9.5H2O*2H(1+); dihydrogen peroxide In acetonitrile at 80℃; for 9h; Inert atmosphere;
1: 13% 2: 77% With [Fe4III(μ-O)2(μ-acetate)6(2,2'-bipyridine)2(H2O)2](NO3-)(OH-); dihydrogen peroxide; acetic acid In water; acetonitrile at 32℃; for 3h; Overall yield = 89 %Spectr.; 2.4. C-H activation analysis by the oxido-acetato-bridged tetraironcomplex (1) General procedure: Conversion of cyclooctane: Cyclooctane (228 mg, 268 ml,2 mmol) was added to a solution of 1 (0.04 mmol) in MeCN:aceticacid (1.5:0.5 ml) in over all catalyst 1: substrate: oxidant0.04:200:500). After the addition of H2O2 (33% in H2O; 454 mL,5.0 mmol), the reaction mixture was heated at 32 °C for 3 h. Themixturewas then allowed to cool to room temperature. The organicphase was extracted with Et2O (3 x 1 ml), washed with brine anddried (MgSO4). After filtration, the solvents of the filtrate wereevaporated (rotary evaporator). The remaining mixture was separatedby column chromatography (silica gel; diethyl ether:pentane 1:20 as eluent) and the product was analyzed by GC-MSusing 1,2-dichlorobenzene as an internal standard.
1: 8% 2: 74% With oxygen; copper diacetate; acetaldehyde In dichloromethane; acetonitrile at 70℃; for 24h; Inert atmosphere;
1: 71% 2: 10.8% With (5,10,15,20-tetrakis(pentafluorophenyl)porphyrinato)iron(III) chloride; oxygen In benzene at 120℃; for 6h; 2.3. Catalytic experiments General procedure: Oxidation of cycloalkanes by molecular oxygen was carried outin the stainless steel batch reactor at 393 K and under the air pressureof 10 atm. Cycloalkane to oxygen molar ratio was set at 6.5.The amount of iron μ-oxo or monomeric iron porphyrin givingthe final concentration 3.3 x 10-5 M of the catalyst in the reactionmixture was dissolved in 1 ml of benzene and added to 60 ml ofcycloalkane. Reactor filled with substrate and the catalyst waspre-treated under the argon flow to remove air and to provide aninert atmosphere. Then the rector was heated to 393 K and airwas introduced. After 6 h of reaction time the oxidation wasstopped by immersing the hot reactor in a cold water bath. Yieldsof products were calculated based on the oxygen quantity in thebatch reactor for all catalytic tests. Reaction products were analyzedusing Agilent Technologies 6890N chromatograph equippedwith Innovax chromatography column (30 m). The yield valueswere verified by an addition of internal standard, chlorobenzene,at the end of the reaction. Cycloalcohol and cycloketone were theonly oxygen-containing products, together with traces of cycloalkanehydroperoxide. The blank experiment confirmed that thecycloalkane was not oxidized by O2 in the absence of catalyst.
1: 68.8% 2: 14.2% With [5,10,15,20-tetrakis(2,6-dichlorophenyl)porphinato]cobalt(II); oxygen at 120℃; for 6h;
1: 66% 2: 34% With [PPh4]2[MnV(N)(CN)4]; tetrabutylammonium periodite; acetic acid In 2,2,2-trifluoroethanol at 23℃; Inert atmosphere;
1: 63% 2: 34% With [PPh4]2[MnV(N)(CN)4]; dihydrogen peroxide; acetic acid In 2,2,2-trifluoroethanol at 23℃; for 5h; Inert atmosphere;
1: 57% 2: 15% With ammonium acetate; chloro(meso-tetrakis(2,6-dichlorophenyl)porphyrinato)manganese(III); dihydrogen peroxide In dichloromethane; acetonitrile for 2h; Ambient temperature;
1: 53% 2: 23% With dihydrogen peroxide; oxalic acid In water; acetonitrile at 60℃; for 8h; Green chemistry; regioselective reaction;
1: 52.3% 2: 6.8% With C48H12F68MnN2O2; oxygen at 119.84℃; for 6h; Autoclave; Green chemistry; 2.3 General procedure for the oxidation of cycloalkanes General procedure: The oxidation of cyclooctane (cyclopentane or cyclohexane) was performed in a stainless steel batch reactor system at 393 K and under the air pressure of 10 atm, with the substrate to oxygen molar ratio set at 6.5. In a typical experiment, 60 mL of substrate containing the amount of catalyst providing a concentration of 3.3×10-4 M was introduced in the deaerated autoclave and the whole system was heated until a temperature of 393 K was reached. Air was then introduced and after 6 h the oxidation products were analyzed by GC Agilent 6890 N equipped with an Innowax (30 m) column. The yield values were verified by addition of an internal standard, chlorobenzene, at the end of the reaction.
1: 51% 2: 6% With tert.-butylhydroperoxide; manganese(II,III) oxide In acetonitrile at 70℃; for 3h; chemoselective reaction;
1: 47% 2: 30% With tert.-butylhydroperoxide In water; acetonitrile at 50℃; for 5h; 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.
1: 46% 2: 29% With 1H-imidazole; sodium periodate; Mn(TDCPP)OAc In dichloromethane for 24h; Ambient temperature;
1: 43% 2: 9% With 1H-imidazole; dihydrogen peroxide In dichloromethane; acetonitrile for 2h; Ambient temperature;
1: 3% 2: 43% With 1H-imidazole; dihydrogen peroxide In dichloromethane; acetonitrile for 2h; Ambient temperature;
1: 9% 2: 43% With 1H-imidazole; dihydrogen peroxide In dichloromethane; acetonitrile at 20℃;
1: 42% 2: 31% With dihydrogen peroxide In water; acetonitrile at 60℃; for 3h;
1: 35% 2: 21 % Chromat. With 1H-imidazole; sodium periodate; MnTPPS-Ad In water; acetonitrile for 8h; Ambient temperature;
1: 25.8% 2: 34.6% With chloro[N,N'-bis(salicylaldehyde)cyclohexanodiminate]iron(III); dihydrogen peroxide; nitric acid In acetonitrile at 20℃; for 3h; 2.4. Catalytic experiments General procedure: The homogeneous phase catalytic studies were performed using 5.00 mmol of cyclohexane, 0.05 mmol of homogeneous catalyst(1 mol% relative to cyclohexane), 0.5 mmol of nitric acid and25 mmol of hydrogen peroxide as sustainable oxidant in 20.00 mlof acetonitrile in batch reactors at room temperature, atmospheric pressure and under constant stirring (1300 rpm) (Scheme 2).Therefore, the ratio of cyclohexane/catalyst/HNO3/H2O2 was,respectively, 100/1/10/500 [18]. The reactions were performed at least twice
1: 33% 2: 12% With 1H-imidazole; dihydrogen peroxide In dichloromethane; acetonitrile at 20℃;
1: 31% 2: 19% With C22H16N4O8V2; dihydrogen peroxide In acetonitrile at 60℃; for 4h; General oxidation procedure General procedure: The liquid phase catalytic oxidations were carried out under air(atmospheric pressure) in a 25 mL round bottom flask equippedwith a magnetic stirrer and immersed in a thermostated oil bathat 80 or 60 C. In a typical experiment, a mixture of 30% H2O2(3 mmol), solvent (3 mL), NaHCO3 (0.25 mmol), chlorobenzene(0.1 g) as internal standard and cis-cyclooctene (1 mmol) wasadded to a flask containing the catalyst 1-8 (1.70 lmol). Thecourse of the reaction was monitored using a gas chromatographequipped with a capillary column and a flame ionization detector.The oxidation products were identified by comparing their retentiontimes with those of authentic samples or alternatively by 1HNMR and GC-Mass analyses. Yields based on the added substratewere determined by a calibration curve. Control reactions werecarried out in the absence of catalyst, H2O2 and NaHCO3 underthe same conditions as the catalytic runs verifying that no products,or only trace yields, were detected.
1: 26% 2: 8.1% With perchloric acid; C13H30N4*Fe(3+)*CF3O3S(1-)*C2H2F3O(1-)*C6H5IO In 2,2,2-trifluoroethanol; acetone at -40℃; for 0.166667h; Inert atmosphere; Schlenk technique; Further stages;
1: 3.7% 2: 21.2% With tert.-butylhydroperoxide; 4 A molecular sieve In benzene at 60℃; for 48h;
1: 21% 2: 35 % Chromat. With 1H-imidazole; sodium periodate; MnTPPS-Ad In water; acetonitrile for 8h; Ambient temperature;
1: 13.6% 2: 11.4% With dihydrogen peroxide; C52H45Cu6Ge8O24*6C3H7NO; trifluoroacetic acid In water; acetonitrile at 50℃; for 3h; Overall yield = 25 percent;
1: 9% 2: 12% Stage #1: Cyclooctan In water-d2 at 20℃; for 0.166667h; Stage #2: In water-d2 at 20℃; for 3h; UV-irradiation;
1: 3% 2: 11% With BaFeO(2.8-x); oxygen at 89.84℃; for 72h;
1: 11.4% 2: 5.5% With dihydrogen peroxide; C16H36Cu6O24Si8*5C3H7NO*0.5H2O; trifluoroacetic acid In water; acetonitrile at 50℃; for 3h; Overall yield = 16.9 percent;
1: 7.9% 2: 5.4% With C11H14FeN3O11S*3H2O; dihydrogen peroxide; nitric acid In water; acetonitrile at 25℃; for 6h; Overall yield = 13.3 %;
1: 29 % Chromat. 2: 15 % Chromat. With cetyldimethylbenzylammonium chloride In dichloromethane at 20℃; for 0.05h;
With lithium perchlorate; acetic acid In water; acetonitrile electrolysis; Yield given. Yields of byproduct given;
With pyridine; tert.-butylhydroperoxide; oxygen; acetic acid at 60℃;
1: 1 % Chromat. 2: 39 % Chromat. With tert.-butylhydroperoxide In benzene for 2h; Ambient temperature;
With pyridine; oxygen; trifluoroacetic acid at 20 - 30℃; electrolyse: i = 14 mA/cm2, anode: platinum, cathode: mercury; Yield given. Yields of byproduct given;
With 2-Picolinic acid; tert.-butylhydroperoxide; ferric nitrate In pyridine; acetic acid for 10h; Ambient temperature; Yield given. Yields of byproduct given;
With iodosylbenzene In dichloromethane; acetonitrile at 20℃; for 2h; Yield given. Yields of byproduct given;
With 1-methyl-1H-imidazole; (5,10,15,20-tetraphenylporphyrinato)manganese(III) chloride; oxygen; acetic acid; zinc In dichloromethane; acetonitrile for 0.5h; Yield given;
With peracetic acid In ethyl acetate for 2h; Ambient temperature; Yield given. Yields of byproduct given;
With ferric picolinate complexes; dihydrogen peroxide In pyridine; water; acetic acid at 0℃; for 18h; Yield given. Yields of byproduct given;
1: 33 % Turnov. 2: 67 % Turnov. With oxygen; isobutyraldehyde In acetonitrile Ambient temperature;
With 18-crown-6 ether; oxygen; acetaldehyde; copper dichloride 1.) CH2Cl2, 20 min, 2.) CH2Cl2, 1 atm, 24 h, 70 deg C; Yield given. Multistep reaction. Yields of byproduct given;
1: 10 % Chromat. 2: 12 % Chromat. With sodium periodate In dichloromethane; water at 80℃; for 15h; Title compound not separated from byproducts;
1: 33 % Turnov. 2: 67 % Turnov. With <bis(salicylidene-N-methyl 3-hydroxypropionate)>cobalt; oxygen; isobutyraldehyde In acetonitrile Ambient temperature;
With tert.-butylhydroperoxide; di-tert-butyl peroxide; oxygen In various solvent(s) at 20℃; for 24h; Yield given;
1: 12 % Chromat. 2: 31 % Chromat. With sodium periodate In dichloromethane; water at 80℃; for 15h; Title compound not separated from byproducts;
1: 53 % Chromat. 2: 6 % Chromat. With iodosylbenzene; chloro<meso-tetra(4-N-methylpyridinio)porphyrinato>manganese(III) tetrachloride (Mn(tmpyp)Cl) on montmorillonite (ClaypMn) In dichloromethane; acetonitrile at 20℃; for 1h; other cyclo- and linear alkanes; various reagents;
With 4-tert-butylpyridine; Mn(tclpp)Cl; dihydrogen peroxide; benzoic acid In dichloromethane at 0℃; for 0.333333h; pH 4.5 - 5.0; other alkanes; various Mn(III)-porphyrins and times;
With 5,10,15,20-tetra(2',6'-dichlorophenyl)porphyrinatoiron(III) chloride; oxygen at 22℃; Irradiation; other iron-porphyrin complexes;
1: 0.95 mmol 2: 0.27 mmol With tert.-butylhydroperoxide; oxygen In acetonitrile at 60℃; for 48h; other hydrocarbons, other solvent, time, temperature; presence of 18O2;
With ferric picolinate complexes; dihydrogen peroxide In pyridine at 0℃; for 18h; functionalization with other catalyst;
1: 20 % Chromat. 2: 36 % Chromat. With 1H-imidazole; 4-vinylpyridine; sodium periodate; manganese(III) 5,10,15,20-tetra(sulfonato)porphyrin In acetonitrile for 8h; Ambient temperature; other alkanes;
With air; tris(μ-oxo)di[(1,4,7-trimethyl-1,4,7-triazanonane)manganese(IV)] hexafluorophosphate; cyclohexanecarbaldehyde In acetonitrile at 60℃; for 8h; reaction course with time, other temperature and reaction time;
With cis-Cyclooctene; 3-chloro-benzenecarboperoxoic acid In dichloromethane at -15℃; for 0.0833333h;
With dihydrogen peroxide In acetonitrile at 25℃; for 1.5h;
1: 8 % Chromat. 2: 77 % Chromat. With tert.-butylhydroperoxide; cis-<Ru(6,6-Cl2bpy)2(OH2)2>(CF3SO3)2 In acetone at 20℃; for 24h;
With peracetic acid In ethyl acetate at 20℃; for 0.25h; Title compound not separated from byproducts;
1: 28 % Chromat. 2: 17 % Chromat. With 1H-imidazole; sodium periodate; Mn(III)meso-(p-sulfonato-Ph)4-β-Br8-porphyrin*Amberl.IRA400 In water; acetonitrile at 20℃; for 10h;
1: 9 % Chromat. 2: 3 % Chromat. With 1H-imidazole; air; tetra-n-butylammonium hydrogen monopersulfate In dichloromethane at 20℃; for 0.05h;
With tert.-butylhydroperoxide; acetic acid In acetonitrile at 30℃;
1: 33 % Chromat. 2: 17 % Chromat. With 1H-imidazole; sodium periodate; Mn(III) tetrakis(4-aminophenyl)porphyrin on polystyrene In water; acetonitrile at 20℃; for 8h;
1: 23 % Chromat. 2: 19 % Chromat. With 1H-imidazole; sodium periodate; Mn(III)TPPS-PSMP In acetonitrile at 20℃; for 8h;
With chromium(VI) oxide; dihydrogen peroxide In acetonitrile at 60℃; for 0.833333h;
1: 51 % Chromat. 2: 5 % Chromat. With 1H-imidazole; [bis(acetoxy)iodo]benzene; [bmim]PF6 In dichloromethane at 20℃;
1: 13 % Chromat. 2: 3 % Chromat. With [bis(acetoxy)iodo]benzene In dichloromethane at 20℃;
1: 65 % Chromat. 2: 19 % Chromat. With 2,6-dichloropyridine N-oxide; tetra-n-butylammonium nitridoosmate(VIII); iron(III) chloride In acetic acid; 1,2-dichloro-ethane at 60℃; for 0.5h;
44 % Chromat. With dihydrogen peroxide; acetic acid In acetonitrile at 20℃; for 5h;
With dihydrogen peroxide In acetonitrile at 70℃; for 4h;
1: 4 % Chromat. 2: 76 % Chromat. With potassium permanganate; boron trifluoride acetonitrile complex In acetonitrile at 24.85℃;
1: 3 %Chromat. 2: 19 %Chromat. With oxygen; acetaldehyde; acetonitrile at 70℃; for 24h;
1: 3 %Chromat. 2: 33 %Chromat. With oxygen; acetaldehyde; acetonitrile In dichloromethane at 25℃; for 48h;
1: 38 % Chromat. 2: 36 % Chromat. With 1H-imidazole; sodium periodate In water; acetonitrile at 20℃; for 0.916667h;
With dihydrogen peroxide In acetonitrile at 25℃; for 0.166667h; Title compound not separated from byproducts.;
1: 68 %Chromat. 2: 22 %Chromat. With tert.-butylhydroperoxide; iron(III) chloride; {tetra-n-butylammonium}{osmiumnitrido(chloro)4} In dichloromethane; acetic acid at 23℃; for 0.0833333h;
Stage #1: Cyclooctan With aluminum(III) nitrate nonahydrate; dihydrogen peroxide In water; acetonitrile at 70℃; Stage #2: With triphenylphosphine In water; acetonitrile
With oxygen at 19.84℃; Neat (no solvent); UV-irradiation;
With tert.-butylhydroperoxide; [(pymox-Me2)2RuCl2]+BF4- In water at 20℃; for 24h;
1: 32 %Chromat. 2: 22 %Chromat. With 1H-imidazole; sodium periodate In water; acetonitrile at 20℃; for 8h;
1: 40 %Chromat. 2: 31 %Chromat. With 1H-imidazole; sodium periodate In water; acetonitrile at 20℃; for 0.5h; Sonication;
1: 31 %Chromat. 2: 6 %Chromat. With 1H-imidazole; manganese(III) meso-tetraphenylporphyrin acetate; dihydrogen peroxide; sodium hydrogencarbonate In water; acetonitrile at 25℃; for 4h;
1: 71 %Chromat. 2: 29 %Chromat. With C8H9N4S(1-)*O2V(1+); dihydrogen peroxide; chlorobenzene In acetonitrile at 80℃; for 5h; chemoselective reaction;
With C42H22FeN9; dihydrogen peroxide In dichloromethane; water; acetonitrile at 20℃; for 5h; chemoselective reaction;
Stage #1: Cyclooctan With tert.-butylhydroperoxide; (OC2H4)(OHC2H4)NC2H4N(C2H4OH)Cu(thiocyanate) In water; acetonitrile at 50℃; for 11h; Stage #2: With triphenylphosphine In water; acetonitrile
1: 52 %Chromat. 2: 26 %Chromat. With dihydrogen peroxide; sodium hydrogencarbonate In water; acetonitrile at 80℃; for 5h;
With dihydrogen peroxide In water at 80℃; for 8h;
1: 42 %Chromat. 2: 28 %Chromat. With sodium periodate; water In acetonitrile for 6h;
1: 54 %Chromat. 2: 6 %Chromat. With Fe(triflate)2(1-(6-methyl-2-pyridylmethyl)-4,7-dimethyl-1,4,7-triazacyclononane); dihydrogen peroxide; acetic acid In water; acetonitrile at 0℃; for 0.666667h;
1: 62 %Chromat. 2: 33 %Chromat. With 1H-imidazole; sodium periodate; 5,10,15,20-tetrakis-(4-aminophenyl) manganese(III) porphyrin chloride In water; acetonitrile at 25℃; for 2h; General procedure for oxidation of alkanes with NaIO4 catalyzed by [Mn(TNH2PP)Cl(at)MWCNT] General procedure: To a mixture of alkane (1 mmol), [Mn(TNH2PP)Cl(at)MWCNT] (350 mg, 0.05 mmol) and imidazole (0.2 mmol) in CH3CN (10 mL) was added a solution of NaIO4 (2 mmol) in H2O (10 mL). The reaction mixture was stirred magnetically at room temperature. The progress of the reaction was monitored by GC. At the end of the reaction, the reaction mixture was diluted with Et2O (20 mL) and filtered. The catalyst was thoroughly washed with Et2O and combined washings and filtrates were purified on silica-gel plates or with a silica-gel column. IR and 1H NMR spectral data confirmed the identities of the products.
1: 33.9 %Chromat. 2: 18.5 %Chromat. With C12H8Mo2N2O16(2-)*2C6H6NO2(1+)*2H2O; oxygen at 119.84℃; for 6h; Autoclave; 2.5 Catalytic activity The oxidation of cyclooctane was performed in a stainless steel batch reactor system at 393K and under the air pressure of 10atm, with the cyclooctane-to-oxygen molar ratio set at 6.5. In a typical experiment, 60ml of substrate containing the amount of catalyst providing a concentration of 3.3×10-4M was introduced in the deaerated autoclave and the whole system was heated until a temperature of 393K was reached. Air was then introduced and after 6h the oxidation products were analyzed by an Agilent 6890N Gas Chromatograph equipped with an Innowax (30m) column. The yield values were verified by addition of an internal standard, chlorobenzene, at the end of the reaction.
With Oxone; [FeIII(1,4,7-trimethyl-1,4,7-triazacyclononane)(acac)Cl]ClO4; sodium hydrogencarbonate In water; acetone at 20℃; for 0.0833333h;
With 1-(2-methyl-1-benzimidazoyl)methyl-4,7-dimethyl-1,4,7-triazacyclononane; water; dihydrogen peroxide In acetonitrile at 20℃; Overall yield = 6.8 %;
With cis-(Cl,Cl)-[Re(p-NC6H4CH3)Cl2(indazole-3-carboxylate)(P(phenyl)3)] methanol solvate; dihydrogen peroxide In water; acetonitrile
1: 45 %Chromat. 2: 30 %Chromat. With sodium periodate In water; acetonitrile at 20℃; for 4h; 2.3 Catalytic experiments General procedure: All of the reactions were carried out at room temperature with magnetic stirring. To a mixture of alkene or alkane (1 mmol), Mn(TPP)ClIm-MIL-101(100 mg) in CH3CN (10 ml), a solution of NaIO4 (2 mmol) in H2O (10 ml) was added. The reaction mixture was stirred at room temperature. The progress of the reaction was monitored by GC. At the end of the reaction, the mixture was diluted with Et2O (20 ml) and filtered. The catalyst was thoroughly washed with Et2O and the combined washings and filtrates were purified on a silica gel plates or a silica gel column to afford the product.
With dihydrogen peroxide In acetonitrile
With Cr2O4(2-)*Cu(2+); dihydrogen peroxide In acetonitrile at 50℃; for 10h;
1: 25 %Chromat. 2: 7 %Chromat. With [Fe(N,N'-dimethyl-N,N'-bis(2-pyridylmethyl)-1,2-diaminoethane)(μ-O)FeCl3]; 3-chloro-benzenecarboperoxoic acid In acetonitrile at 20℃; for 1h; Inert atmosphere;
With dihydrogen peroxide In acetonitrile at 40℃; for 1.5h;
With rac-tris(1,10-phenanthroline)copper(II); dihydrogen peroxide In water at 70℃; for 3h; Autoclave; Catalytic reaction General procedure: The liquid-phase oxidation of cycloalkane with H2O2 (30% in aqueous solution) was carried out under a stirring condition in a sealed autoclave. A typical reaction mixture is as follows: 0.05 g catalyst, 10 mL solvent, 9.5 mmol substrate, and 38 mmol H2O2 (30% in aqueous solution). Unless otherwise stated, the reaction temperature is 70 °C and time is 3 h. After reaction, the liquid product was separated by centrifugation and analyzed by a GC-7890F gas chromatograph equipped with a polyethylene glycol packed column and a flame ionization detector with benzyl chloride as an internal standard.
With bismuth (III) nitrate pentahydrate; dihydrogen peroxide; nitric acid In water; acetonitrile at 60℃;
1: 8.9 %Chromat. 2: 7.1 %Chromat. With [Cu44-(N,N,N',N'-tetrakis(2-hydroxyethyl)ethylenediamine(-2H)))(μ5-(N,N,N',N'-tetrakis(2-hydroxyethyl)ethylenediamine(-2H)))(salicylic acid(-2H))2]*10H2O; dihydrogen peroxide; trifluoroacetic acid In water; acetonitrile at 50℃; for 3h; Overall yield = 16 %Chromat.;
1: 12.3 %Chromat. 2: 7 %Chromat. With [Cu44-(N,N,N',N'-tetrakis(2-hydroxyethyl)ethylenediamine(-H)))2(phenylmalonic acid(-H))2(H2O)]*7.5H2O; dihydrogen peroxide; trifluoroacetic acid In water; acetonitrile at 50℃; for 3h; Overall yield = 19.3 %Chromat.;

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YieldReaction ConditionsOperation in experiment
1: 34.3% 2: 16.6% With 1,2-phenylenediamine molybdenum(VI) oxide; oxygen at 119.84℃; for 6h; Autoclave; 3 Catalytic Investigation The liquid-phase oxidation of cycloalkanes (cyclopentane, cyclohexane or cyclooctane) was performed in a stainlees steel batch reactor system at the optimum temperature of 393 K and under the pressure of 10 atm. with the reagents molar ratio CnH2n (where n = 5, 6, 8):O2 = 13:2. A Teflon-lined reactor of 1 L volume equipped with a magnetic stirrer was used. In a typical experiment, molybdenum based catalyst having the concentration of 3.3 x 10-4 M was introduced into the reaction mixture. The catalyst together with the substrate were closed in the air-free autoclave and were heated together with the whole system until temperature of 393 K was reached. In due time air was added to the hot reaction mixture in such amount that final pressure of 10 atm was obtained and the reaction started. After 6 h of reaction time the oxidation was stopped by immersing the hot reactor in a cold water bath. Reaction products (cycloketone and cycloalcohol) were analyzed by means of Agilent Technologies 6890 N gas chromatograph equipped with Innowax (30 m) column in the presence of chlorobenzene as internal standard. Amounts of CO and CO2 were determined chromatographically using Perkin-Elmer Clarus 500 with methanizer.
1: 6.3% 2: 24.9% 3: 5.3% With cobalt(II) 5,10,15,20-tetra(4'-chlorophenyl)porphyrinate; oxygen at 120℃; for 48h; Autoclave; 2; 4; 9 Example 9 1.0 mg of 5,10,15,20-tetrakis(p-chlorophenyl)porphyrin cobalt (II) was dissolved in 50.0 g of cyclooctane in a 100 mL stainless steel autoclave with a tetrafluoroethylene liner to block the high pressure. kettle. The mixture was heated to 120 ° C with stirring, passed through O2 to 1.0 MPa, and stirred at 120 ° C under a pressure of 1.0 MPa O2 for 48.0 h, and cooled to room temperature with stirring in an ice water bath. Turn on the autoclave, The obtained reaction mixture was filtered, and the obtained solid was washed with 3×10 mL of cyclooctane, and dried under vacuum at 60 ° C to give 4.91 g of white solid as a suberic acid, yield 6.3%. The filtrate obtained by filtration is subjected to vacuum distillation, and 14.81 g of a fraction of 70 °C to 80 °C (20 mmHg) is obtained, which is cyclooctyl ketone, and the yield is 24.9%; A distillate of 3.06 g of 120 °C to 130 °C (22 mm Hg) was obtained, which was cyclooctanol in a yield of 5.3%; and unreacted cyclooctane was recovered by rectification.
With air; manganese(II) acetate; N-hydroxy-4-dodecyloxycarbonylphthalimide In ethanol at 100℃; for 14h;
With oxygen; N–hydroxysaccharin In various solvent(s) at 80℃; for 1.5h;
With cobalt(III) acetylacetonate; oxygen; N–hydroxysaccharin at 80℃; for 1.5h;

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YieldReaction ConditionsOperation in experiment
94% With oxygen; sodium nitrite In trifluoroacetic acid at 0 - 20℃; for 5h;
94% With oxygen; trifluoroacetic acid; sodium nitrite at 0 - 20℃; for 5.25h; 11 An operation was conducted in the same manner as in Example 2 except that cyclohexanol was replaced by an alicyclic secondary alcohol compound or an alicyclic ketone compound, both shown in Table 2 as a raw material compound. The results are shown in Table 2.
89% Stage #1: cyclooctanol With Oxone; ruthenium(III) chloride monohydrate In water at 70℃; for 8h; Stage #2: In ethanol Cooling;
86% With dihydrogen peroxide In water; acetonitrile at 90℃; for 11.5h; Green chemistry;

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