2. 1-Cyclohexylpropan-2-one by Asch

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85%

With [Pd(CH3CN)4]*[BF4]2; (diacetoxyiodo)benzene; water; nitrobenzene; p-benzoquinone in dimethyl sulfoxide

T=35°C; Wacker Oxidation; 48 h; Sealed tubeDarkness;

Bigi, Marinus A.; White, M. Christina

Journal of the American Chemical Society, 2013 , vol. 135, # 21 p. 7831 - 7834 Title/Abstract Full Text View citing articles Show Details

68%

With oxygen; copper(l) chloride; palladium dichloride in water; DMFA

T=55°C; Wacker Oxidation; P=760.051 Torr; 24 h; regioselective reaction;

Annadi, Krishna; Wee, Andrew G. H.

Journal of Organic Chemistry, 2016 , vol. 81, # 3 p. 1021 - 1038 Title/Abstract Full Text View citing articles Show Details

Rx-ID: 35668644 Find similar reactions

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Rx-ID: 38996304 Find similar reactions

With bis(benzonitrile)palladium(II) dichloride; AgNO2; CuCl2·2H2O; oxygen in nitromethane; tert-butyl alcohol

T=20°C; P=760.051 Torr; 6 h; Overall yield = 75 percent; Hide Experimental Procedure

CALIFORNIA INSTITUTE OF TECHNOLOGY; WICKENS, ZACHARY K.; MORANDI, BILL; GRUBBS, ROBERT H.; SKAKUJ, KACPER; BRONNER, SARAH

Patent: US2014/316149 A1, 2014 ; Location in patent: Page/Page column 0140-0149; 0155-0164; 0166-0168; 0175 ; Title/Abstract Full Text Show Details

3.3; 3.5:Example 3.1 General Procedures

General procedure: Example 3.1 General Procedures Example 3.1.1 Procedure (A) for Larger-Scale (0.5 Mmol) Oxidation of Aliphatic Alkenes (Isolation) [0140] PdCl2(PhCN)2 (0.06 mmol, 0.023 g), CuCl2*2H2O (0.06 mmol, 0.0102 g) and AgNO2 (0.03 mmol, 0.0046 g) were weighed into a 20 mL vial charged with a stir bar. The vial was sparged for 2 minutes with oxygen (1 atm, balloon). Premixed and oxygen saturated tert-BuOH (7.5 mL) and MeNO2 (0.5 mL) was added followed by the alkene (0.5 mmol) were added in that order via syringe. The solution was saturated with oxygen by an additional 45 seconds of sparging. The reaction was then allowed to stir at room temperature for 6 hours. Next, the reaction was quenched by addition to water (ca. 50 mL) and extracted three times with dichloromethane (ca. 25 mL). The combined organic layers were subsequently washed with a saturated solution of NaHCO3 and dried over Na2SO4. The solvent was removed under reduced pressure and the desired aldehyde product was purified using flash chromatography (pentane/ether). Selectivity was determined from 1H NMR analysis of the

unpurified mixture by ratio of the aldehydic 1H signal to the most clear signal from the methyl ketone (usually the methyl group). Long relaxation delays (d1=15) were applied due to the long T1 of the aldehydic proton signal. Example 3.1.2 Procedure (B) for Smaller-Scale (0.2 Mmol) Oxidation of 1-Dodecene (GC Analysis) [0141] PdCl2(PhCN)2 (0.024 mmol, 0.0092 g), CuCl2*2H2O (0.024 mmol, 0.0041 g) and AgNO2 (0.012 mmol, 0.0018 g) were weighed into a 2 dram screw-cap vial charged with a stir bar. The vial was sparged for 45 seconds with oxygen (1 atm, balloon) then subsequently tridecane (0.00246 mmol, 6 μL), tert-BuOH (3 mL), MeNO2 (0.2 mL) and 1-dodecene (0.2 mmol, 44.4 μL) were added in that order via syringe. The solution was saturated with oxygen by an additional 45 seconds of sparging. The reaction was then allowed to stir at room temperature for 6 hours. Next, an aliquot (ca. 0.2 mL) was injected into a 2 mL vial containing an estimated 1 mL of premixed EtOAc/pyridine solution (3:1) to quench the reaction. The resulting solution was subsequently subjected to GC analysis to determine yield and selectivity. Example 3.1.3 Procedure (C) for Small-Scale (0.2 Mmol) Oxidation of Alkenes (NMR Analysis) [0142] PdCl2(PhCN)2 (0.024 mmol, 0.0092 g), CuCl2.2H2O (0.024 mmol, 0.0041 g) and AgNO2 (0.012 mmol, 0.0018 g) were weighed into a 2 dram screw-cap vial charged with a stir bar. The vial was sparged for 45 seconds with oxygen (1 atm, balloon) then subsequently tert-BuOH (3 mL), MeNO2 (0.2 mL) and alkene (0.2 mmol) were added in that order via syringe. The solution was saturated with oxygen by an additional 45 seconds of sparging. The reaction was then allowed to stir at room temperature for 6 hours. Next, the reaction mixture was diluted with water (ca. 20 mL) and subsequently extracted three times with CDCl3, dried with Na2SO4 and concentrated under reduced pressure for 1H NMR analysis. Immediately prior to NMR analysis nitrobenzene was added as an internal standard. The resulting solution was subsequently subjected to 1H NMR analysis to determine yield and selectivity by ratio of the aldehydic 1H signal to the most clear signal from the methyl ketone (usually the methyl group). Long relaxation delays (d1=15) were applied due to the long t1 of the aldehydic proton signal. Example 3.1.4 Procedure (D) for Stoichiometric Oxidation of 1-Dodecene (GC Analysis) [0143] PdCl2(PhCN)2 (0.024 mmol, 0.0092 g), CuCl2.2H2O (0.024 mmol, 0.0041 g) and AgNO2 (0.012 mmol, 0.0018 g) were weighed into a 2 dram screw-cap vial charged with a stir bar. The vial was sparged for 45 seconds with oxygen (1 atm, balloon) then subsequently tridecane (0.00246 mmol, 6 μL), tert-BuOH (3 mL), MeNO2 (0.2 mL) and 1-dodecene (0.024 mmol, 5.3 μL) were added in that order via syringe. The solution was saturated with oxygen by an additional 45 seconds of sparging. The reaction was then allowed to stir at room temperature for 3 hours and 30 minutes. Next, an aliquot (ca. 0.2 mL) was injected into a 2 mL vial containing an estimated 1 mL of premixed EtOAc/pyridine solution (3:1) to quench the reaction. The resulting solution was subsequently subjected to GC analysis to determine yield and selectivity. Example 3.1.5 Procedures for Variation of Oxygen Atmosphere [0144] A series of experiments to determine the effect of oxygen atmosphere were conducted, the results being shown in the following Table 1: Based on these data, and without being necessarily bound by the correctness of any particular theory or statement, it appeared that oxygen was the terminal oxidant and sole stoichiometric reagent in this system. Although reaction sealed under air resulted in acceptable yield (60percent, see Table 1), the rate and conversion improved significantly under an oxygen atmosphere. Further increase in oxygen pressure (3 atm) did not provide increased efficiency but did marginally increase the selectivity. [TABLE-US-00001] TABLE 1 Oxygen atmosphere variation Overall yield entry Conditions (aldehyde yield) selectivity 1 no O2 (argon) 12 (10) 80percent 2 air (sealed) 60 (48) 79percent 3 air (open) 38 (27) 71percent 4 O2 (1 atm) 80 (63) 79percent 5 O2 (3 atm) 68 (58) 84percent [0145] Entry 1: Conducted as described in procedure B except using a balloon filled with argon (1 atm) in place of a balloon filled with oxygen. [0146] Entry 2: Conducted as described in procedure B except the reaction was never exposed to pure molecular oxygen. [0147] Entry 3: Conducted as described in procedure B except the reaction was never exposed to pure molecular oxygen and the vial was left uncapped. [0148] Entry 4: Conducted as described in procedure B with no deviation. [0149] Entry 5: Conducted in an open vial placed inside a Fischer porter bottle connected to an oxygen tank and adjusted to 3 atm O2. Example 3.2 Effect of Reaction Parameters (FIG. 3A) [0155] Various redox catalysts, ligands, redox catalysts, palladium sources and a wide variety of additives were investigated. Each of the type of palladium and copper complexes, and the types of oxygen-centered radical species were found to play an important role in the overall performance of the catalytic system, as did the choice of solvent. Removal of any of these components results in dramatically poorer conversion, selectivity, or both. [0156] In one variation of Procedure D, experiments were conducted with the omission of either copper or palladium. The GC was monitored over 3 hours and 30 minutes. When palladium was omitted: no conversion was observed. When copper was omitted: 33percent yield (combined aldehyde and ketone) was observed with 53percent ketoneselectivity. As a reference point, the analogous reaction with DMF/water and no AgNO2 has proceeded to complete conversion with complete ketone selectivity within this time. The results are shown in FIG. 3B. [0157] Removal of copper from the process provided only traces of products. Exposure of alkene to stoichiometric palladium and silver nitrite, however, also provided incomplete oxidation and poor selectivity, suggesting a more intimate role of the copper salt than a simple redox catalyst for palladium (FIG. 3B). Furthermore, stoichiometric copper dichloride and silver nitrite (no palladium) provided no conversion of the alkene. Thus, it appears that both palladium and copper are crucial metals for the efficient stoichiometric oxidation of alkenes. Ag(I) salts have been shown to be non-innocent additives (potential oxidants) in palladium-catalyzed reactions. However, if AgNO2 was replaced by NaNO2, a similar reaction outcome was observed with marginally lower selectivity (FIG. 3C). This strongly implied that nitrite was the critical component of the co-catalyst, not Ag(I). [0158] Detailed reaction profiles employing various quantities of AgNO2 (FIG. 3D) were generated to study the effect of time on the reaction. Increased loading of AgNO2 correlated with a faster reaction, implying a rate dependence on AgNO2 concentration. A similar overall yield of aldehyde was obtained using both 12 and 6 mol percent AgNO2, with slightly improved aldehyde yield using 6 mol percent. Interestingly, even 2 mol percent AgNO2 provided useful yields of aldehyde after a longer reaction time. Omission of AgNO2 led to a process not exceeding 20percent overall yield. [0159] In a related series of experiments, Procedure B was used to measure the progress of the reaction with time. Time points were collected with a Freeslate (formerly Symyx) software system at the given times and quenched with a 3:1 mixture of EtOAc and pyridine, followed by GC analysis using tridecane as an internal standard. Reaction temperature is further maintained at 20° C. throughout the course of the reaction. Variation of nitrite loading was accomplished with no further deviation from protocol B. After GC analysis, the data was processed and graphed using Microsoft Excel. See again FIG. 3D. [0160] In contrast to previous attempts by others to develop and aldehyde-selective Wacker-type oxidation, that have been plagued by low yields and loss of selectivity over the course of the reaction, in the present experiments, tests with 1-dodecene showed the selectivity stabilized after 5percent conversion and became relatively independent of both yield and time. See FIG. 3E. [0161] Other nitrite sources, including organic and inorganic derivatives, were evaluated by Procedure B. Catalytic AgNO2 was found to provide the highest selectivity among nitrite sources (see Table 2). [TABLE-US-00002] TABLE 2 Nitrite sources (obtained by procedure B) Overall yield entry Conditions (aldehyde yield) selectivity 1 tert-BuONO 75 (41) 55percent 2 n-BuONO 76 (34) 45percent 3 NOBF4 73 (42) 59percent 4 Pd(NO2)Cl(MeCN)2 80 (21) 29percent 5 AgNO2 80 (63) 79percent 6 NaNO2 82 (61) 75percent [0162] From these studies, co-catalytic nitrite salts were found to provide unparalleled reactivity in the presence of palladium and copper. Intriguingly, when the reaction was conducted in an open vessel, both yield and selectivity were significantly worse than when sealed under air. (see Table 1). [0163] The introduction of a small amount of a polar co-solvent, nitromethane, both increased homogeneity of the reaction mixture and enabled room temperature reaction. Once optimized, the new conditions (PdCl2(PhCN)2 (12 mol percent), CuCl2*2H2O (12 mol percent), AgNO2 (6 mol percent) in tert-BuOH/MeNO2 (15:1) under 1 atm oxygen) oxidized 1-dodecene to dodecanal in 63percent yield (see also FIG. 2A/2B and FIG. 3A). Example 3.5 Characterizations of Products in Table 3 [0166] Dodecanal (Table 1, Entry 2) [0168] 61percent yield obtained using procedure A. 1H NMR (500 MHz, CDCl3) δ 9.76 (t, J=1.9 Hz, 1H), 2.43 (td, J=7.4, 1.9 Hz, 2H), 1.64 (tt, J=7.5, 7.5 Hz, 2H), 1.49-1.18 (m, 16H), 0.97-0.77 (t, J=6.8, 3H). Spectral data were in accordance with a commercial sample.

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A: 58 %Chromat. B: 39 %Chromat.

With (x)C4H8O*(x)C18H15P*Ru; hydrogen in tetrahydrofuran

T=30°C; P=15001.5 Torr; 2.5 h; AutoclaveGlovebox; Reagent/catalyst;

Castelbou, Jessica Llop; Bres-Femenia, Emma; Blondeau, Pascal; Chaudret, Bruno; Castilln, Sergio; Claver, Carmen; Godard, Cyril

ChemCatChem, 2014 , vol. 6, # 11 p. 3160 - 3168 Title/Abstract Full Text View citing articles Show Details

A: 30 %Chromat. B: 70 %Chromat.

With (x)C4H8O*(x)C28H28P2*Ru; hydrogen in tetrahydrofuran

T=30°C; P=15001.5 Torr; 5 h; AutoclaveGlovebox;

Castelbou, Jessica Llop; Bres-Femenia, Emma; Blondeau, Pascal; Chaudret, Bruno; Castilln, Sergio; Claver, Carmen; Godard, Cyril

ChemCatChem, 2014 , vol. 6, # 11 p. 3160 - 3168 Title/Abstract Full Text View citing articles Show Details

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B: 60%

With bis(benzonitrile)palladium(II) dichloride; AgNO2; CuCl2·2H2O; nitromethane; oxygen; tert-butyl alcohol

T=20°C; Wacker Oxidation; P=760.051 Torr; 6 h; Overall yield = 75 percent;

Wickens, Zachary K.; Morandi, Bill; Grubbs, Robert H.

Angewandte Chemie - International Edition, 2013 , vol. 52, # 43 p. 11257 - 11260 Angew. Chem., 2013 , vol. 125, # 43 p. 11467 - 11470 Title/Abstract Full Text View citing articles Show Details

With ethanol; iodine; mercury(II) oxide

Erwaermen mit alkoh. Kalilauge und verd. Schwefelsaeure;

de Resseguier

Bulletin de la Societe Chimique de France, 1914 , vol. <4> 15, p. 178 Full Text View citing articles Show Details

With diethyl ether; iodine; mercury(II) oxide

Behandeln mit Silbernitrat in Aether;

de Resseguier

Bulletin de la Societe Chimique de France, 1914 , vol. <4> 15, p. 178 Full Text View citing articles Show Details

With methanol; iodine; mercury(II) oxide

Erwaermen mit alkoh. Kalilauge und verd. Schwefelsaeure;

de Resseguier

Bulletin de la Societe Chimique de France, 1914 , vol. <4> 15, p. 178 Full Text View citing articles Show Details

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Rx-ID: 9415345 Find similar reactions

92%

With hydrogen in tetrahydrofuran

T=24.84°C; P=30003 Torr; chemoselective reaction;

Gonzalez-Galvez, David; Lara, Patricia; Rivada-Wheelaghan, Orestes; Conejero, Salvador; Chaudret, Bruno; Philippot, Karine; Van Leeuwen, Piet W.N.M.

Catalysis Science and Technology, 2013 , vol. 3, # 1 p. 99 - 105 Title/Abstract Full Text View citing articles Show Details

100 % Chromat.

With hydrogen; K5PPdW11O39/C in various solvent(s) T=200°C; P=22502.3 Torr; 4 h;

Kogan, Vladimir; Aizenshtat, Zeev; Neumann, Ronny

New Journal of Chemistry, 2002 , vol. 26, # 3 p. 272 - 274 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 36631007 Find similar reactions

With silica-alumina; nickel in α-n-hexadecene

T=159.84°C; 4 h; Inert atmosphere;

Wang, Xingyu; Rinaldi, Roberto

Angewandte Chemie - International Edition, 2013 , vol. 52, # 44 p. 11499 - 11503 Angew. Chem., 2013 , vol. 125, # 44 p. 11713 - 11717,5 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 4389183 Find similar reactions

81%

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Stage #1: methyllithium With copper (I) cyanide in diethyl ether

T=0°C; 0.0833333 h; Inert atmosphere; Stage #2: 4-carboxymethyl cyclohexane in diethyl ether

T=0 - 20°C; 15 h; Inert atmosphere;

Genna, Douglas T.; Posner, Gary H.

Organic Letters, 2011 , vol. 13, # 19 p. 5358 - 5361 Title/Abstract Full Text View citing articles Show Details

in diethyl ether

Carenini; Carissimi; Gentili; Grumelli; Picciola; Ravenna

Arzneimittel-Forschung/Drug Research, 1976 , vol. 26, # 12 p. 2127 - 2136 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 30038538 Find similar reactions

With hexafluoroantimonic acid; [Au(1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene)hydroxide]; water

T=120°C; 24 h;

Nun, Pierrick; Ramon, Ruben S.; Gaillard, Sylvain; Nolan, Steven P.

Journal of Organometallic Chemistry, 2011 , vol. 696, # 1 p. 7 - 11 Title/Abstract Full Text View citing articles Show Details

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Synthesize Find similar Rx-ID: 28782254 Find similar reactions

A: 40%

Hara, Keiichi; Tosaki, Shin-ya; Gnanadesikan, Vijay; Morimoto, Hiroyuki; Harada, Shinji; Sugita, Mari; Yamagiwa, Noriyuki; Matsunaga, Shigeki; Shibasaki, Masakatsu

Tetrahedron, 2009 , vol. 65, # 26 p. 5030 - 5036 Title/Abstract Full Text View citing articles Show Details

With (S)-La-Li3-(binaphthoxide)3; C42H36LaLi3O12 in tetrahydrofuran

T=-20°C; Retro-nitroaldol reaction; 15 h; optical yield given as percent eeenantioselective reaction;

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Rx-ID: 3528201 Find similar reactions

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56%

With potassium permanganate; potassium acetate; Manganese (II) acetate; acetic acid

T=70°C; addition of KMnO4, 4-10 h;

Linker, Ursula; Kersten, Berthold; Linker, Torsten

Tetrahedron, 1995 , vol. 51, # 36 p. 9917 - 9926 Title/Abstract Full Text View citing articles Show Details

40%

With sodium peroxodisulphate; silver nitrate in water

8 h; Heating;

Citterio, Attilio; Ferrario, Francesco; Bernardinis, Silvia De

Journal of Chemical Research, Miniprint, 1983 , # 12 p. 2669 - 2683 Title/Abstract Full Text Show Details

43 %Chromat.

Shiraishi, Yasuhiro; Tsukamoto, Daijiro; Hirai, Takayuki

Organic Letters, 2008 , vol. 10, # 14 p. 3117 - 3120 Title/Abstract Full Text View citing articles Show Details

in water

T=40°C; 6 h; PhotoirradiationInert atmosphere;

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Synthesize Find similar Rx-ID: 10344869 Find similar reactions

With (R)-1,1'-bi-2-naphthol/La,Li heterobimetallic; (R)-6,6'-dimethoxybiphenyl-2,2'-diol/La,Li in tetrahydrofuran

T=-20°C; 15 h;

Tosaki, Shin-Ya; Hara, Keiichi; Gnanadesikan, Vijay; Morimoto, Hiroyuki; Harada, Shinji; Sugita, Mari; Yamagiwa, Noriyuki; Matsunaga, Shigeki; Shibasaki, Masakatsu

Journal of the American Chemical Society, 2006 , vol. 128, # 36 p. 11776 - 11777 Title/Abstract Full Text View citing articles Show Details

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Synthesize Find similar Rx-ID: 9949970 Find similar reactions

A: 17% B: 8%

Saito, Shinichi; Dobashi, Naotomo; Wakatsuki, Yasuo

Chemistry Letters, 2005 , vol. 34, # 4 p. 504 - 505 Title/Abstract Full Text View citing articles Show Details

With carbon monoxide; trifluoroacetic acid; tri-ruthenium(0)dodecacarbonyl in water; isopropyl alcohol

T=120°C; P=760 Torr; 12 h;

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Rx-ID: 9950836 Find similar reactions

Stage #1: With PyBH2I in dichloromethane

T=20°C; Stage #2: With sodium hydroxide; dihydrogen peroxide in methanol; dichloromethane

T=0 - 20°C; Title compound not separated from byproducts;

Clay, Julia M.; Vedejs, Edwin

Journal of the American Chemical Society, 2005 , vol. 127, # 16 p. 5766 - 5767 Title/Abstract Full Text View citing articles Show Details

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Synthesize Find similar Rx-ID: 9677858 Find similar reactions

With hydrogen; iridium

T=75°C; P=3040 Torr;

Fonseca, Gledison S.; Scholten, Jackson D.; Dupont, Jairton

Synlett, 2004 , # 9 p. 1525 - 1528 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 9073711 Find similar reactions

49%

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With copper(l) iodide; boron trifluoride diethyl etherate in tetrahydrofuran

T=-30 - 0°C; 1 h;

Hayes, Jerome F.; Shipman, Michael; Twin, Heather

Journal of Organic Chemistry, 2002 , vol. 67, # 3 p. 935 - 942 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 8737171 Find similar reactions

50%

Stage #1: With copper(l) iodide; boron trifluoride diethyl etherate in tetrahydrofuran

T=-30 - 0°C; Ring cleavage; Stage #2: in tetrahydrofuran

Hydrolysis; Further stages.;

Hayes; Shipman; Twin

Chemical Communications, 2000 , # 18 p. 1791 - 1792 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 3941383 Find similar reactions

Maruoka; Concepcion; Yamamoto

Synthesis, 1994 , # SPEC. ISS. p. 1283 - 1290 Title/Abstract Full Text View citing articles Show Details

in methanol; diethyl ether

T=0°C; 2 h; other organoaluminum promotors; Product distribution;

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Rx-ID: 4029944 Find similar reactions

Maruoka; Concepcion; Yamamoto

Synthesis, 1994 , # SPEC. ISS. p. 1283 - 1290 Title/Abstract Full Text View citing articles Show Details

in methanol; dichloromethane

T=25°C; 18 h; other organoaluminum promotors; Product distribution;

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Rx-ID: 4029945 Find similar reactions

With trimethylaluminum in dichloromethane

T=-78°C; 1 h; Yield given. Yields of byproduct given;

Maruoka; Concepcion; Yamamoto

Synthesis, 1994 , # SPEC. ISS. p. 1283 - 1290 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 2827279 Find similar reactions

With sodium hydroxide; dihydrogen peroxide in tetrahydrofuran

2 h; Ambient temperature;

Brown, Herbert C.; Imai, Toshiro; Bhat, N. G.

Journal of Organic Chemistry, 1986 , vol. 51, # 26 p. 5277 - 5282 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 2948980 Find similar reactions

With titanium(III) chloride in tetrahydrofuran; water

Ambient temperature;

Barton, Derek H.R.; Togo, Hideo; Zard, Samir Z.

Tetrahedron, 1985 , vol. 41, # 23 p. 5507 - 5516 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 1999408 Find similar reactions

72%

With tert-butyl peroxyacetate

T=95°C; 16 h;

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Jaouhari, Rabih; Filliatre, Claude; Villenave, Jean-Jacques

Canadian Journal of Chemistry, 1983 , vol. 61, p. 2295 - 2298

Title/Abstract Full Text Show Details

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Rx-ID: 3248533 Find similar reactions

With sulfuric acid in methanol

1 h; Ambient temperature; Yield given;

Miller, R. B.; Al-Hassan, M. I.; McGarvey, G.

Synthetic Communications, 1983 , vol. 13, # 12 p. 969 - 976 Title/Abstract Full Text Show Details

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Rx-ID: 19451674 Find similar reactions

Multi-step reaction with 3 steps 1: 99 percent / 1) sec-butyllithium / tetrahydrofuran / 1.) -78 deg C, 0.5 h, 2.) RT, 1 h 2: m-chloroperoxybenzoic acid / CH2Cl2 / 1.)0 deg C, 15 min, 2.) RT, 6 h 3: aq. H2SO4 / methanol / 1 h / Ambient temperature View Scheme

Miller, R. B.; Al-Hassan, M. I.; McGarvey, G.

Synthetic Communications, 1983 , vol. 13, # 12 p. 969 - 976 Title/Abstract Full Text Show Details

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Multi-step reaction with 2 steps 1: m-chloroperoxybenzoic acid / CH2Cl2 / 1.)0 deg C, 15 min, 2.) RT, 6 h 2: aq. H2SO4 / methanol / 1 h / Ambient temperature View Scheme

Rx-ID: 19463599 Find similar reactions

Miller, R. B.; Al-Hassan, M. I.; McGarvey, G.

Synthetic Communications, 1983 , vol. 13, # 12 p. 969 - 976 Title/Abstract Full Text Show Details

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Rx-ID: 1999409 Find similar reactions

A: 55%

Jaouhari, Rabih; Maillard, Bernard; Filliatre, Claude; Villenave, Jean-Jacques

Synthesis, 1982 , # 9 p. 760 - 763 Title/Abstract Full Text Show Details

T=130°C; 2.5 h;

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Rx-ID: 1999410 Find similar reactions

Jaouhari, R.; Filliatre, C.; Maillard, B.; Villenave, J.J.

Tetrahedron, 1982 , vol. 38, # 21 p. 3137 - 3142 Title/Abstract Full Text View citing articles Show Details

T=130°C; 2.5 h; variation of time and temperature; Product distributionMechanism;

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A: 55%

T=130°C; 2.5 h; Further byproducts given;

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Jaouhari, R.; Filliatre, C.; Maillard, B.; Villenave, J.J.

Tetrahedron, 1982 , vol. 38, # 21 p. 3137 - 3142 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 1999412 Find similar reactions

Jaouhari, R.; Filliatre, C.; Maillard, B.; Villenave, J.J.

Tetrahedron, 1982 , vol. 38, # 21 p. 3137 - 3142 Title/Abstract Full Text View citing articles Show Details

in acetone

T=130°C; 2.5 h; Yield given. Further byproducts given. Yields of byproduct given;

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With di-tert-butyl peroxide

T=130°C; 20 h; Yield given. Yields of byproduct given;

Jaouhari, R.; Filliatre, C.; Maillard, B.; Villenave, J.J.

Tetrahedron, 1982 , vol. 38, # 21 p. 3137 - 3142 Title/Abstract Full Text View citing articles Show Details

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Synthesize Find similar Rx-ID: 2532209 Find similar reactions

in cyclohexane

T=130°C; 2.5 h; Further byproducts given. Yields of byproduct given;

Jaouhari, R.; Filliatre, C.; Maillard, B.; Villenave, J.J.

Tetrahedron, 1982 , vol. 38, # 21 p. 3137 - 3142 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 3523776 Find similar reactions

With di-tert-butyl peroxide

T=130°C; 20 h; Product distribution;

Jaouhari, R.; Filliatre, C.; Maillard, B.; Villenave, J.J.

Tetrahedron, 1982 , vol. 38, # 21 p. 3137 - 3142 Title/Abstract Full Text View citing articles Show Details

With di-tert-butyl peroxide

T=130°C; 20 h; Yields of byproduct given;

Jaouhari, R.; Filliatre, C.; Maillard, B.; Villenave, J.J.

Tetrahedron, 1982 , vol. 38, # 21 p. 3137 - 3142 Title/Abstract Full Text View citing articles Show Details

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C: 0.18 mol

With di-tert-butyl peroxide in cyclohexane

T=130°C; 20 h; Yields of byproduct given;

Jaouhari, R.; Filliatre, C.; Maillard, B.; Villenave, J.J.

Tetrahedron, 1982 , vol. 38, # 21 p. 3137 - 3142 Title/Abstract Full Text View citing articles Show Details

Synthesize Find similar With mercury(II) diacetate in trifluoroacetic acid

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Rx-ID: 1093239 Find similar reactions

Martin,S.F.; Chou,T.

Tetrahedron Letters, 1978 , p. 1943 - 1946 Full Text View citing articles Show Details

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Rx-ID: 1418530 Find similar reactions

(i) Ni catalyst, (ii) aq. HCl; Multistep reaction;

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Tamao,K. et al.

Chemistry Letters, 1976 , p. 1239 - 1242 Full Text View citing articles Show Details

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Rx-ID: 6396130 Find similar reactions

exo-7-Norcarylmethylketon (2), H2, Pd/C;

Schultz

Journal of Organic Chemistry, 1971 , vol. 36, p. 383 Full Text View citing articles Show Details

Cyclohexanessigsaeurechlorid, Methylmagnesiumiodid/CdCl2;

Nagao et al.

Kogyo Kagaku Zasshi, 1969 , vol. 72, p. 236 Chem.Abstr., 1969 , vol. 70, # 114372 Full Text Show Details

aus Triphenylphosphinacetylmethylen (Zitat 13);

Nagao et al.

Kogyo Kagaku Zasshi, 1969 , vol. 72, p. 236 Chem.Abstr., 1969 , vol. 70, # 114372 Full Text Show Details

B-Cyclohexyl-9-borabicyclo<3.3.1>nonan, α-Bromaceton;

Cyclohexen, Aceton;

Brown et al.

Journal of the American Chemical Society, 1969 , vol. 91, p. 6852 Full Text View citing articles Show Details

Hajek et al.

Tetrahedron Letters, 1974 , p. 3193 Full Text View citing articles Show Details

Andreew et al.

Biol. Akt. Soedin., 1968 , p. 79,84 Chem.Abstr., 1970 , vol. 72, # 3076 Full Text Show Details

Cyclohexylacetylchlorid, 1.) CH2N2, Ether, 2.) HI, CHCl3;

Stodola et al.

Biochemical Journal, 1964 , vol. 93, p. 92,96 Full Text Show Details

1-Cyclohexyl-propan-2-ol, N-Brom-succinimid, Py., CCl4, Oxidation;

Alkenylborol 3(R'=cyclohexyl, R=methyl), H2O2 / NaOH;

Brown,H.C.; Gupta,S.K.

Journal of the American Chemical Society, 1975 , vol. 97, p. 5249 - 5255 Full Text View citing articles Show Details

Acn., Cyclohexen, PbO2;

Hajek; Malek

Synthesis, 1976 , p. 315 Full Text Show Details

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Rx-ID: 1012369 Find similar reactions

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Hegedus,L.S.; Stiverson,R.K.

Journal of the American Chemical Society, 1974 , vol. 96, p. 3250 - 3254 Full Text View citing articles Show Details

(i) Ni(CO)4, (ii) /BRN= 1900797/; Multistep reaction;

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Rx-ID: 26628277 Find similar reactions

With H(1+); H2O in N,N-dimethyl-formamide 25-60°C;

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Hegedus, L. S.; Stiverson, R. K.

Journal of the American Chemical Society, 1974 , vol. 96, p. O325 - O3254 Full Text Show Details

Gmelin Handbook: Ni: Org.Verb.2, 2.3.1.7, page 305 - 310 Full Text Show Details

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Rx-ID: 1070205 Find similar reactions

Zweifel,G. et al.

Journal of the American Chemical Society, 1971 , vol. 93, p. 3395 - 3399 Full Text View citing articles Show Details

(i) dicyclohexylborane, THF, (ii) aq. H2O2, aq. NaOH; Multistep reaction;

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Rx-ID: 1302584 Find similar reactions

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Barltrop,J.A.; Thomson,A.

Journal of the Chemical Society [Section] C: Organic, 1968 , p. 155 - 166 Full Text View citing articles Show Details

Irradiation;

Synthesize Find similar T=525°C;

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Rx-ID: 765085 Find similar reactions

Bailey; Daly

Journal of Organic Chemistry, 1957 , vol. 22, p. 1189,1192 Full Text Show Details

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Rx-ID: 303248 Find similar reactions

With methyl-magnesium iodide

Chiang

Journal of the Chinese Chemical Society (Peking), 1951 , vol. 18, p. 65,69, 74 Full Text Show Details

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Rx-ID: 21999999 Find similar reactions

Multi-step reaction with 2 steps 1: palladium; ethanol / Hydrogenation 2: methyl magnesium iodide View Scheme

Chiang

Journal of the Chinese Chemical Society (Peking), 1951 , vol. 18, p. 65,69, 74 Full Text Show Details

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Rx-ID: 554748 Find similar reactions

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With aluminium oxide-zinc oxide-copper (II)-oxide contact

T=350°C; P=15445.7 Torr;

Ipatieff; Haensel

Journal of Organic Chemistry, 1942 , vol. 7, p. 189,196 Full Text Show Details

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Rx-ID: 5714548 Find similar reactions

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Ipatieff; Haensel

Journal of Organic Chemistry, 1942 , vol. 7, p. 189,196 Full Text Show Details

T=350°C; P=15445.7 Torr;

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Rx-ID: 7976808 Find similar reactions

Guerbet

Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1917 , vol. 164, p. 953 Bulletin de la Societe Chimique de France, 1918 , vol. <4> 23, p. 72 Full Text Show Details

Synthesize Find similar With hydrogen; palladium

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Rx-ID: 156488 Find similar reactions

Wallach

Justus Liebigs Annalen der Chemie, 1912 , vol. 394, p. 372 Chem. Zentralbl., 1908 , vol. 79, # I p. 637,639 Full Text View citing articles Show Details

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Rx-ID: 6800761 Find similar reactions

Wallach

Justus Liebigs Annalen der Chemie, 1912 , vol. 394, p. 372 Chem. Zentralbl., 1908 , vol. 79, # I p. 637,639 Full Text View citing articles Show Details

Hydrogenation;

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Rx-ID: 22402056 Find similar reactions

Multi-step reaction with 2 steps 1: sodium ethylate / 0 °C 2: hydrogen; palladium View Scheme

Wallach

Justus Liebigs Annalen der Chemie, 1912 , vol. 394, p. 372 Chem. Zentralbl., 1908 , vol. 79, # I p. 637,639 Full Text View citing articles Show Details

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Rx-ID: 760242 Find similar reactions

T=-10°C;

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Darzens; Rost

Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1911 , vol. 153, p. 773 Full Text Show Details

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Rx-ID: 22155459 Find similar reactions

Multi-step reaction with 3 steps 1: nickel / Hydrogenation 2: thionyl chloride 3: -10 °C View Scheme

Darzens; Rost

Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1911 , vol. 153, p. 773 Full Text Show Details

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Rx-ID: 22160753 Find similar reactions

Multi-step reaction with 2 steps 1: thionyl chloride 2: -10 °C View Scheme

Darzens; Rost

Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1911 , vol. 153, p. 773 Full Text Show Details

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Rx-ID: 276796 Find similar reactions

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With ethanol

Hell; Schaal

Chemische Berichte, 1909 , vol. 42, p. 2232 Full Text Show Details

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Rx-ID: 276799 Find similar reactions

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Hell; Schaal

Chemische Berichte, 1909 , vol. 42, p. 2232 Full Text Show Details

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Rx-ID: 6396131 Find similar reactions

With acid

Hell; Schaal

Chemische Berichte, 1909 , vol. 42, p. 2232 Full Text Show Details

With alkali

Hell; Schaal

Chemische Berichte, 1909 , vol. 42, p. 2232 Full Text Show Details

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Synthesize Find similar Rx-ID: 7980839 Find similar reactions zerfaellt bei gewoehnlicher Temp.;

Hell; Schaal

Chemische Berichte, 1909 , vol. 42, p. 2232 Full Text Show Details

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Rx-ID: 6396132 Find similar reactions

With anhydrous calcium acetate

durch Destillation;

Wallach

Justus Liebigs Annalen der Chemie, 1907 , vol. 353, p. 302 Chem. Zentralbl., 1907 , vol. 78, # II p. 53 Full Text Show Details

Synthesize Find similar With chromic acid

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Rx-ID: 409727 Find similar reactions

Freundler

Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1906 , vol. 142, p. 344 Bulletin de la Societe Chimique de France, 1906 , vol. <3> 35, p. 548 Full Text Show Details