[ CAS No. 1193-47-1 ] {[proInfo.proName]}

Name: 1193-47-1|2,2-Dimethylcyclohexanone|95%
Brand: Ambeed
SKU: A739998
Rating: 97 (40 reviews)

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COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 1193-47-1 ]

CAS No. :	1193-47-1	MDL No. :	MFCD00134382
Formula :	C₈H₁₄O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	KNSPBSQWRKKAPI-UHFFFAOYSA-N
M.W :	126.20	Pubchem ID :	136929
Synonyms :

Safety of [ 1193-47-1 ]

Signal Word:	Danger	Class:	3
Precautionary Statements:	P210-P403+P235	UN#:	1224
Hazard Statements:	H225	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 1193-47-1 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 1193-47-1 ]
Downstream synthetic route of [ 1193-47-1 ]

[ 1193-47-1 ] Synthesis Path-Upstream 1~3

1
[ 590-66-9 ]
[ 2979-19-3 ]
[ 1193-46-0 ]
[ 932-01-4 ]
[ 767-12-4 ]
[ 1193-47-1 ]
[ 4255-62-3 ]

Reference： [1] Journal of the American Chemical Society, 2015, vol. 137, # 50, p. 15833 - 15842

2
[ 1193-47-1 ]
[ 24247-77-6 ]

Reference： [1] Patent: WO2011/144584, 2011, A1,

3
[ 1193-47-1 ]
[ 540-69-2 ]
[ 77287-34-4 ]
[ 24247-77-6 ]

Reference： [1] Bulletin de la Societe Chimique de France, 1957, p. 600,606

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Yield	Reaction Conditions	Operation in experiment
64%	With sodium tetrahydroborate In methanol at 20℃;
	With diethyl ether; sodium
	With lithium aluminium tetrahydride

	With sodium tetrahydroborate In isopropyl alcohol at 25℃; for 20h;
	With lithium aluminium tetrahydride In diethyl ether
	With sodium tetrahydroborate
	With sodium tetrahydroborate In isopropyl alcohol at 25℃; for 20h;
	With 1,4-dihydronicotinamide adenine dinucleotide ΔG(excit.); HLAD, Tris-HCl buffer, pH=8.5;
	With sodium tetrahydroborate In methanol at 0℃;

Yield	Reaction Conditions	Operation in experiment
94%	With tetra-N-butylammonium tribromide In methanol; dichloromethane at 20℃; for 2.5h; Inert atmosphere; Schlenk technique;
75%	With hydrogen bromide; bromine In acetic acid
70%	With bromine In chloroform at 0℃; for 2h;

Yield	Reaction Conditions	Operation in experiment
42%	With hydroxylamine hydrochloride; sodium hydroxide In ethanol; water for 48h; Reflux;	21.1 Example 21.2-Cyclopropyl-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (2,2-dimethyl-cyclohexyl)- amideStep 1In a 50 mL flask 2,2-dimethylcyclohexanone (0.50 g, 4.0 mmol) was dissolved in EtOH (10 mL). Hydroxylamine hydrochloride (1.04 g, 15.0 mmol), H20 (4 mL), and 20% aqueous NaOH (4 mL) were added and the reaction mixture was heated at reflux for 2 d then cooled to room temperature overnight. The solvent was removed under reduced pressure. The residue was taken up in H20 and filtered to collect 203 mg (36%) of (E/Z)-2,2- dimethylcyclohexanone oxime as a white solid. The filtrate was extracted with CH2C12 (2x). The combined organics were dried over Na2S04 and concentrated to afford a further 34 mg (6%) of product as a white solid.
	With hydroxylamine hydrochloride; sodium hydrogencarbonate In ethanol for 24h; Heating;
	With hydroxylamine hydrochloride; sodium acetate In ethanol; water at 100℃;

[ CAS No. 1193-47-1 ] {[proInfo.proName]}

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[ 1193-47-1 ] Synthesis Path-Upstream 1~3

[ 1193-47-1 ] Synthesis Path-Downstream 1~88

Related Functional Groups of
[ 1193-47-1 ]

Aliphatic Cyclic Hydrocarbons

Ketones

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	With tetrachloromethane; N-Bromosuccinimide im UV-Licht;
	With bromine In chloroform
	Multi-step reaction with 2 steps 1: N-Bromosuccinimide; toluene-4-sulfonic acid / dichloromethane / 15 h / 0 °C / Reflux 2: N-ethyl-N,N-diisopropylamine / acetonitrile / 25 h / 28 °C / Irradiation; Inert atmosphere

Yield	Reaction Conditions	Operation in experiment
85%	With N-Bromosuccinimide; toluene-4-sulfonic acid In dichloromethane at 0℃; for 15h; Reflux;
	With dichloromethane; bromine

Yield	Reaction Conditions	Operation in experiment
	With sulfuric acid for 1h; Heating;
	With toluene-4-sulfonic acid at 90℃; for 9h;

Yield	Reaction Conditions	Operation in experiment
81%	With sodium amide In tetrahydrofuran for 2h; Heating;
	With potassium <i>tert</i>-butylate

Yield	Reaction Conditions	Operation in experiment
59%	With boron trifluoride diethyl etherate In benzene at 40℃; for 1h;
	With boron trifluoride diethyl etherate In benzene at 50℃; for 1h;

Yield	Reaction Conditions	Operation in experiment
	Yield given. Multistep reaction;
	Multi-step reaction with 2 steps 1: MeLi / tetrahydrofuran / 0.5 h / -15 - 20 °C 2: 1.) MnCl₂, LiCl / 1.) THF, rt., 1 h; 2.) THF/DMSO, rt., 1 h
	Multi-step reaction with 2 steps 1: 71 percent / TiCl₄ / CH₂Cl₂ / 1 h / -23 °C 2: 98 percent / W-2 Raney nickel / acetone; ethanol / 2 h / 20 °C

Yield	Reaction Conditions	Operation in experiment
75%	With hydrogenchloride In methanol at -10℃;
	With hydrogenchloride In methanol for 12h; Ambient temperature;

Yield	Reaction Conditions	Operation in experiment
94%	With zinc(II) iodide In dichloromethane at 25℃; for 2h;
94%	In dichloromethane at 25℃; for 2h;

Yield	Reaction Conditions	Operation in experiment
85%	In tetrahydrofuran at -78℃; for 2h;
72%
	In tetrahydrofuran at 25℃; for 2h; Inert atmosphere; Cooling with ice;

	In tetrahydrofuran at 25℃; for 3h; Inert atmosphere; Cooling with ice;
27.3 g	In tetrahydrofuran at 0 - 20℃; for 2.5h; Inert atmosphere; Schlenk technique;

Yield	Reaction Conditions	Operation in experiment
	With diisopinocamphenylchloroborane at 25℃; for 12h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
	With 2,2'-iminobis[ethanol]; (-)-diisopinocamphenylborane chloride 1) neat, room t., 12 h; 2) ethyl ether, 2 h; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;
	With diphenylsilane; potassium carbonate 1.) THF, -40 deg C, 26 h, 2.) MeOH; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;

	With potassium 9-O-(1,2:5,6-di-O-isopropylidene-α-D-glucofuranosyl)-9-boratabicyclo<3.3.1>nonane In tetrahydrofuran at -50℃; for 48h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
	Stage #1: 2,2-dimethyl-cyclohexanone With diphenylsilane In tetrahydrofuran at -40℃; for 26h; Stage #2: With methanol; potassium carbonate In tetrahydrofuran at 20℃; for 4h; Title compound not separated from byproducts;
	With [dichloro((S)-2,2'-bis(di-4-tolylphosphino)-1,1'-binaphthyl)(α-picolylamino)ruthenium(II)]; potassium <i>tert</i>-butylate; hydrogen In ethanol at 25℃; for 5h; Title compound not separated from byproducts;
78 % ee	With C₄₄H₄₇N₂O₃PRuS₃⁽²⁺⁾*2BF₄^(1-); potassium <i>tert</i>-butylate; hydrogen; dimethyl sulfoxide In methanol at 25℃; for 24h; Autoclave; Overall yield = 94 %; Overall yield = 117 mg; enantioselective reaction;

Yield	Reaction Conditions	Operation in experiment
78%	With sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0 - 20℃; for 18h;	General procedure: NaHCO3 (836 mg, 9.95 mmol, 1.99 equiv) was added to a solution of ketone 2a/2 (5.0 mmol, 1.0 equiv) in CH2Cl2 (15 mL). The resulting suspension was placed in an ice bath and m-CPBA (949 mg, 5.5 mmol, 1.1 equiv) was added in portions. The mixture was subsequently stirred for 18 h while allowing to warm to room temperature. The mixture was partitioned between CH2Cl2 (25 mL) and saturated aqueous NaHCO3 (60 mL). Layers were separated and the aqueous layer was extracted with CH2Cl2 (3 × 25 mL). The combined organic fractions were dried (Na2SO4) and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (petroleum ether/EtOAc) to give product 3a/3.
	With sodium acetate; 3-chloro-benzenecarboperoxoic acid In dichloromethane

Yield	Reaction Conditions	Operation in experiment
97%	With sodium amide In tetrahydrofuran for 2h; Heating;
83%	Stage #1: 2-Methylcyclohexanone With sodium hydride In tetrahydrofuran; mineral oil for 1.5h; Inert atmosphere; Reflux; Stage #2: With 1,1,1,3,3,3-hexamethyl-disilazane In tetrahydrofuran; mineral oil for 0.25h; Inert atmosphere; Reflux; Stage #3: methyl iodide In tetrahydrofuran; mineral oil at 0 - 25℃; for 3h; Inert atmosphere;	4.1 In this example 4, 2,2-dimethyl-1 -ethynyl-1 -cyclohexanol was prepared as follows. In a first step, to a 1 L two-neck flask equipped with a water-cooled condenser, was added NaH (60% in mineral oil, 16 gram) and 350 mL anhydrous THF under N2. To this suspension, was added 2-methylcyclohexanone (44 ml). The 2- methylcyclohexanone and the other starting materials were commercially available from Sigma Aldrich. The mixture was heated to reflux for 1 .5 hours. H gas was released in the first 20 minutes), then HMDS (hexamethyldisilazane, 1 1 .4 mL) was added, and the mixture was refluxed for another 15 minutes. After cooling to 0°C, methyl iodide (30 mL) was slowly added to the flask, and the resulting reaction was highly exothermic. The flask was allowed to warm up to room temperature and stirred for 3 hours. THF was removed with a rotary evaporator. To the residue, was added diethyl ether (150 mL). The mixture was filtered, and ether was removed with the rotary evaporate to give the crude, which was further purified by vacuum distillation to give 2,2- dimethylcyclohexanone as a colorless liquid (37.6 gram, 83% yield).
79%	Stage #1: 2-Methylcyclohexanone With sodium hydride In tetrahydrofuran for 1.5h; Inert atmosphere; Reflux; Stage #2: With 1,1,1,3,3,3-hexamethyl-disilazane In tetrahydrofuran for 0.25h; Inert atmosphere; Reflux; Stage #3: methyl iodide In tetrahydrofuran at 0 - 23℃; for 3h; Inert atmosphere;

Yield	Reaction Conditions	Operation in experiment
92%	With zinc(II) iodide In dichloromethane at 25℃; for 8h;
92%	In dichloromethane at 25℃; for 8h;

Yield	Reaction Conditions	Operation in experiment
	Yield given. Multistep reaction;
	Multi-step reaction with 2 steps 1: 85 percent / sodium amide, Fe(NO₃)3 / diethyl ether / 2.33 h 2: 45 percent / POCl₃ / pyridine / 2 h / 100 °C
	Multi-step reaction with 2 steps 1: liquid NH₃; diethyl ether 2: 300 - 320 °C / 60 Torr / durch Destillation ueber AlPO₄

Yield	Reaction Conditions	Operation in experiment
1: 1.7% 2: 0.8% 3: 94%	With manganese(II) bromide; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; lithium hexamethyldisilazane In tetrahydrofuran for 4h; Ambient temperature;
1: 94% 2: 0.8% 3: 1.7%	With manganese(II) bromide; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; lithium hexamethyldisilazane In tetrahydrofuran at 22℃; for 4h;

Yield	Reaction Conditions	Operation in experiment
1: 5% 2: 1% 3: 89%	With manganese(II) bromide; lithium hexamethyldisilazane In tetrahydrofuran for 14h; Ambient temperature;
1: 89% 2: 1% 3: 5%	With manganese(II) bromide; lithium hexamethyldisilazane In tetrahydrofuran at 22℃; for 14h;

75%	With potassium hydride
55%	Stage #1: 2-Methylcyclohexanone With sodium hydride In tetrahydrofuran; mineral oil for 1h; Schlenk technique; Inert atmosphere; Reflux; Stage #2: With 1,1,1,3,3,3-hexamethyl-disilazane In tetrahydrofuran; mineral oil for 0.25h; Schlenk technique; Inert atmosphere; Reflux; Stage #3: methyl iodide In tetrahydrofuran; mineral oil at 0 - 20℃; for 2.16667h; Schlenk technique; Inert atmosphere;
33%	With sodium amide In tetrahydrofuran Reflux;
	With triethyl borane; potassium hydride THF, room temp.; Yield given. Multistep reaction;
	With sodium hydride Yield given;
	With triethyl borane; potassium hydride 1.) THF, 12 h, 25 deg C; 2.) 10 h, THF; Yield given. Multistep reaction;
	Stage #1: 2-Methylcyclohexanone With sodium hydride In toluene at 100℃; for 2h; Stage #2: methyl iodide In toluene at 60℃; for 4h; Further stages.;
	Stage #1: 2-Methylcyclohexanone With potassium hydride In tetrahydrofuran at 20℃; for 0.5h; Stage #2: With triethyl borane In tetrahydrofuran at 20℃; for 16h; Stage #3: methyl iodide In tetrahydrofuran for 8h;	2, 2-Dimethyl-cyclohexanon (Vorprodukt für Beispiel C-26) Eine Suspension von Kaliumhydrid (5. 5 mmol) und 2- Methylcyclohexanon (5 mmol) in trockenem Tetrahydrofuran (10 ml) wird während 30 min bei Raumtemperatur gerührt. Man tropft langsam Triethylboran (6. 25 mmol) zu und rührt 16 Stunden bei Raumtemperatur. Nach Zugabe von Methyliodid wird weitere 8 Stunden gerührt, die Reaktion anschliessend mit gesättigter wässriger Ammoniumchlorid-Lösung gequencht und zweimal mit Diethylether extrahiert. Die vereinigten organischen Phasen werden über Natriumsulfat getrocknet und im Vakuum zur Trockene eingeengt und ergeben die Titelverbindung, welche ohne ohne Aufreinigung weiter umgesetzt werden kann (JACS 1985, 107, 19, 5391-5396).
	Stage #1: 2-Methylcyclohexanone With sodium hydride In tetrahydrofuran; mineral oil for 1h; Inert atmosphere; Reflux; Stage #2: methyl iodide In tetrahydrofuran; mineral oil at 0 - 20℃; for 3.16667h; Inert atmosphere;
	Stage #1: 2-Methylcyclohexanone With sodium amide In tetrahydrofuran for 2h; Inert atmosphere; Reflux; Stage #2: methyl iodide In tetrahydrofuran at 5 - 70℃; for 1h;	12 Example 12: 2,2-dimethylcyclohexanone synthesis Take 100mL three-necked flask, removable nitrogen three times, was added through a dropping funnel was added 42mLTHF,10.9mL2- Methyl cyclohexanone (89mmol), nitrogen, was added in portions 3.9gNaNH2 (100mmol, added six points) was stirred and heated under reflux for 2h, yellow viscous solution. Cooled to 5 ,Was slowly added 7.76mLCH3I (125mmol), the solution became white viscous loaded, heated to reflux (70 About) 1h. Filtered, washed with ether and the white residue, and the combined organic phases. The organic phase was washed with saturated NH4ClSolution, saturated NaCl, then dried with anhydrous NaSO4 rotary evaporation give crude compound 10,And then distilled under reduced pressure to give a colorless liquid 7.4258g, without further purification, direct investment next step.
	Stage #1: 2-Methylcyclohexanone With sodium hydride In tetrahydrofuran Reflux; Inert atmosphere; Stage #2: methyl iodide In tetrahydrofuran at 0 - 20℃; Inert atmosphere;
	Stage #1: 2-Methylcyclohexanone With sodium hydride In toluene; mineral oil at 100℃; for 2h; Stage #2: methyl iodide In toluene; mineral oil at 60℃; for 2h;	1 Step 1. To a stirred suspension of NaH (5.12 g, 134 mmol of 60% mineral oil dispersion) in dry toluene (180 mL) was added 2-methylcyclohexan-1-one (10.00 g, 89.2 mol) dropwise during 2 h at 100 °C. To this was added CH3I (19.00 g, 134 mol) dropwise over 2 h at 60 °C. The mixture was stirred for an additional 2 h at 60 °C. After cooling, a mixture of NaOMe (10.60 g, 196 mmol) and HCO2Me (11.2 g, 152 mmol) were added to the mixture at 5°C, and the reaction mixture stirred for 12 h at room temperature before being poured into ice water (100 mL). The aqueous layer was acidified with 10% HCl aqueous and extracted with ether. The combined organic phases were washed with brine, dried over MgSO4 and concentrated to afford (E)-6-(hydroxymethylene)-2,2- dimethylcyclohexan-1-one (9.00 g, 65%) as a brown oil. LCMS: LC retention time 2.09 min. MS (ESI) m/z 155 [M+H]+.

Yield	Reaction Conditions	Operation in experiment
78%	With sodium hydride In benzene for 22h; Heating;
	With sodium hydride Yield given;
	With sodium hydride

Yield	Reaction Conditions	Operation in experiment
85%	With pyridine; hydroxylamine hydrochloride In ethanol
49%	With hydroxylamine hydrochloride; sodium acetate In ethanol; water at 20 - 60℃;

Yield	Reaction Conditions	Operation in experiment
100%	Stage #1: 2,2-dimethyl-cyclohexanone With lithium diisopropyl amide In tetrahydrofuran at -78℃; Stage #2: N,N-phenylbistrifluoromethane-sulfonimide In tetrahydrofuran at -78℃;	Intermediate T12T12.1 [0378] j-Dimethyl-1-cyclohexen-1-yl trifluoromethanesulfonate (T12.1).To a solution of 2,2-dimethylcyclohexanone (2.00 g, 16 mmol, commercially available from Sigma-Aldrich, St. Louis, MO, USA) in THF (35 mL) at -78°C was added dropwise LDA (9 mL, 18 mmol, 2.0 M). The resulting solution was stirred at -78°C for 20 minutes. A solution of N-phenyl-bis(trifluoromethane sulfonimide) (6 g, 17 mmol) in THF (15 mL) was then slowly added at -78°C. The reaction mixture was then allowed to warm to 23°C over 3 hours. And then was concentrated in vacuo. The reaction was diluted with brine and extracted three times with EtOAc. The combined organic layers were dried over anhydrous MgSO4 and filtered. The organic solvent was removed under reduced pressure, and the product was purified on silica gel (0- 10% EtOAc in hexanes) to provide T12.1 as a clear oil (4.1 g, 100%).
100%	Stage #1: 2,2-dimethyl-cyclohexanone With lithium diisopropyl amide In tetrahydrofuran at -78℃; Stage #2: N,N-phenylbistrifluoromethane-sulfonimide In tetrahydrofuran at -78 - 23℃;	T14A; T14B [0419] 6,6-Dimethyl-1-cyclobexen-1-yl trifluoromethanesulfonate (T14.1).To a solution of 2,2-dimethylcyclohexanone (2.00 g, 16 mmol, commercially available from Aldrich) in THF (35 mL) at -78°C was added dropwise LDA (9 mL, 18 mmol, 2.0 M). The resulting solution was stirred at -78°C for 20 minutes. A solution of N-phenyl- bis(trifluoromethane sulfonimide) (6 g, 17 mmol) in THF (15 mL) was then added slowly at -78°C. The reaction mixture was allowed to warm to 23°C over 3 hours and the reaction was then concentrated in vacuo. The reaction was diluted with brine and extracted three times with EtOAc. After drying over anhydrous magnesium sulfate and filtering, the organic solvent was removed under reduced pressure and the product was then purified on silica gel (0-10% EtOAc in hexanes) T14.1 as a clear oil (4.1 g, 100%).
55%	Stage #1: 2,2-dimethyl-cyclohexanone With n-butyllithium; diisopropylamine In tetrahydrofuran at -78℃; for 1h; Inert atmosphere; Stage #2: N,N-phenylbistrifluoromethane-sulfonimide In tetrahydrofuran at -78 - 20℃; for 2.5h; Inert atmosphere;

Yield	Reaction Conditions	Operation in experiment
	In chloroform at -12℃; for 120h; Title compound not separated from byproducts;
	In chloroform at -24℃; for 96h; Title compound not separated from byproducts;
	In chloroform at -12℃; for 120h; Title compound not separated from byproducts.;

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 100 percent / NaOEt / pentane / 24 h / Heating 2: 80 percent / lithium diisopropylamide / tetrahydrofuran / 0.5 h / -25 - 20 °C 3: 93 percent / LiAlH₄ / diethyl ether / 0.75 h / Heating
	Multi-step reaction with 3 steps 1: sodium hydride / tetrahydrofuran / 15 h / Reflux; Inert atmosphere 2: lithium diisopropyl amide / tetrahydrofuran / 16 h / -25 - 20 °C / Inert atmosphere 3: lithium aluminium tetrahydride / diethyl ether; tetrahydrofuran / 0.75 h / 0 °C / Inert atmosphere

[ CAS No. 1193-47-1 ] {[proInfo.proName]}

Quality Control of [ 1193-47-1 ]

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Application In Synthesis of [ 1193-47-1 ]

[ 1193-47-1 ] Synthesis Path-Upstream 1~3

[ 1193-47-1 ] Synthesis Path-Downstream 1~88

Related Functional Groups of [ 1193-47-1 ]

Aliphatic Cyclic Hydrocarbons

Ketones

Precautionary Statements-General

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Related Functional Groups of
[ 1193-47-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: sodium hydride 2: diisobutylaluminium hydride 3: (S)-proline / CH₂Cl₂ / 20 °C
	Multi-step reaction with 5 steps 1: sodium hydride 2: LiAlH₄ 3: pyridinium chlorochromate 4: (S)-proline / CH₂Cl₂ / 20 °C

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: sodium hydride 2: diisobutylaluminium hydride 3: (S)-proline / CH₂Cl₂ / 20 °C 4: NaBH₄ / CH₂Cl₂
	Multi-step reaction with 6 steps 1: sodium hydride 2: LiAlH₄ 3: pyridinium chlorochromate 4: (S)-proline / CH₂Cl₂ / 20 °C 5: NaBH₄ / CH₂Cl₂

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 85 percent / tetrahydrofuran / 2 h / -78 °C 2: 76 percent / potassium bisulfate / 0.17 h / 150 °C
	Multi-step reaction with 2 steps 1: 72 percent 2: 87 percent / CuSO₄*5H₂O / benzene / 2 h / Heating
	Multi-step reaction with 2 steps 1: tetrahydrofuran / 3 h / 25 °C / Inert atmosphere; Cooling with ice 2: copper(II) sulfate / benzene / 20 h / Reflux

	Multi-step reaction with 2 steps 1.1: magnesium; iodine / tetrahydrofuran / 2 h / Inert atmosphere; Reflux 1.2: 4 h / 20 °C / Inert atmosphere 2.1: copper(II) sulfate / hexane / 10 h / Inert atmosphere; Dean-Stark; Reflux
	Multi-step reaction with 2 steps 1: tetrahydrofuran / 2.5 h / 0 - 20 °C / Inert atmosphere; Schlenk technique 2: copper(II) sulfate / benzene / Reflux; Dean-Stark; Inert atmosphere; Schlenk technique
	Multi-step reaction with 2 steps 1: tetrahydrofuran / 2 h / Inert atmosphere 2: copper(II) sulfate / benzene / 24 h / 90 °C / Inert atmosphere; Dean-Stark

Yield	Reaction Conditions	Operation in experiment
76%	With C₁₂H₁₂F₆O₄Pt; chlorobenzene; p-benzoquinone; barium(II) oxide at 80℃; for 12h; Inert atmosphere; Glovebox;
	Multi-step reaction with 2 steps 1: 1.) potassium hydride / 1.) DME, 20 min, 2.) DME 2: ¹O₂ / acetone-d6 / 23 °C
	Multi-step reaction with 2 steps 1: 75 percent / bromine, HBr / acetic acid 2: 72 percent / LiBr, Li₂CO₃ / dimethylformamide / 7 h / 130 °C

	Multi-step reaction with 2 steps 1: <i>N</i>-bromo-succinimide; CCl₄ / im UV-Licht 2: 190 - 200 °C
	Multi-step reaction with 2 steps 1: bromine / chloroform / 2 h / 0 °C 2: magnesium oxide / N,N-dimethyl-formamide / 3 h / 140 °C / Inert atmosphere

Yield	Reaction Conditions	Operation in experiment
1: 14 %Chromat. 2: 29 %Chromat. 3: 18 %Chromat. 4: 11 %Chromat.	With [(S,S)-Fe(1,1'-bis((5-(2,6-bis(trifluoromethyl)phenyl)pyridin-2-yl)methyl)-2,2'-bipyrrolidine)(acetonitrile)<SUB>2</SUB>](SbF<SUB>6</SUB>)<SUB>2 </SUB>; dihydrogen peroxide; acetic acid In water; acetonitrile at 20℃; for 0.5h;
1: 16 %Chromat. 2: 35 %Chromat. 3: 17 %Chromat. 4: 13 %Chromat.	With [(S,S)-Fe(1,1'-bis((5-(2,6-bis(trifluoromethyl)phenyl)pyridin-2-yl)methyl)-2,2'-bipyrrolidine)(acetonitrile)<SUB>2</SUB>](SbF<SUB>6</SUB>)<SUB>2 </SUB>; dihydrogen peroxide; acetic acid In water; acetonitrile at 20℃; for 0.5h;	2.6.1 Reaction 6. Oxidation of 1,1-Dimethylcyclohexane GC Yield Data. Run 1: 16% RSM, 16% S2, 35% S3a, 17% S3b, 13% S4, 5.3:1 distal:proximal. Run 2: 24% RSM, 14% S2, 28% S3a, 20% S3b, 11% S4, 5.8:1 distal:proximal. Run 3: 23% RSM, 13% S2, 26% S3a, 18% S3b, 10% S4, 5.6:1 distal:proximal. Average RSM: 21±4%. Average S2: 14±2%. Average S3a: 29±5%. Average S3b: 18±2%. Average S4: 11±2%. Average distal:proximal: 5.6±0.3:1. Data for (S,S)-Fe(PDP) (1) have been previously reported (Chen and White, Science 2010, 327, 566). (0224) (0225) 4,4-dimethylcyclohexanone (S2). 1,1-dimethylcyclohexane (S1) (33.7 mg, 0.3 mmol, 1.0 equiv, Sigma-Aldrich) was reacted with (S,S)-Fe(CF3-PDP) (2) according to Method A with nitrobenzene (60 mol %) added as an internal standard. Yields were determined by GC analysis of the crude reaction mixture after reaction completion. All product yields are calibrated for response factors relative to starting material, rounded to the nearest whole number and the average of three runs. 1H NMR (400 MHz, CDCl3) δ 2.34 (t, J=6.8 Hz, 4H), 1.67 (app t, J=7.2 Hz, 4H), 1.09 (s, 6H). (0226) (0227) 3,3-dimethylcyclohexanone (S3a). 1H NMR (400 MHz, CDCl3) δ 2.26 (app t, J=6.8 Hz, 2H), 2.15 (s, 2H), 1.91-1.84 (m, 2H), 1.59-1.57 (m, 2H), 0.97 (s, 6H). (0228) (0229) 3,3-dimethylcyclohexanol (S3b). 1H NMR (500 MHz, CDCl3) δ 3.78-3.68 (m, 1H), 1.98-1.91 (m, 1H), 1.71-1.57 (m, 2H), 1.49-1.37 (m, 1H), 1.32-1.24 (m, 2H), 1.13-1.01 (m, 2H), 0.95 (s, 3H), 0.89 (s, 3H). These spectral data match those reported in the literature (Kamata et al., Nature Chem. 2010, 2, 478). (0230) (0231) 2,2-dimethylcyclohexanone (S4). 1H NMR (400 MHz, CDCl3) δ 2.39 (app t, J=6.8 Hz, 2H), 1.86-1.80 (m, 2H), 1.77-1.70 (m, 2H), 1.68-1.64 (m, 2H), 1.11 (s, 6H).

Yield	Reaction Conditions	Operation in experiment
91%	Stage #1: propargyl alcohol With potassium hydroxide In water at 45℃; Stage #2: 2,2-dimethyl-cyclohexanone In water at 40℃;
11.2 g	With potassium hydroxide In water at 45℃;	13 Example 13: Compound 11 synthesis Take 100mL three-necked flask, propargyl alcohol was added 14.4mL (0.29mol) and 13.2mL of water, stirring,Join 35.57gKOH (0.63mol), exothermic phenomenon, the system becomes sticky, additional 6mL water, dissolvedLiquid clarification. The crude compound 20g (0.16mol, containing 70% 2,2-dimethyl-cyclohexanone) was added 10System, 45 stirred overnight. Quenched with 200mL of water was added, extracted with ethyl acetate completely, the organic layer was washed with60mL saturated ammonium chloride solution was washed with saturated NaCl wash, washed with water, dried over anhydrous sodium sulfate, concentrated, columnChromatography to give a white solid 11.2g, yield 55.4%

Yield	Reaction Conditions	Operation in experiment
40%	With C₂₈H₂₈N₂O₄S₄; water; palladium diacetate; potassium trifluoroacetate; trifluoroacetic acid In 1,4-dioxane at 80℃; for 12h;
40%	With C₂₈H₂₈N₂O₄S₄; water; palladium diacetate; potassium trifluoroacetate; trifluoroacetic acid In 1,4-dioxane at 80℃; for 12h; Sealed tube;	6.2 General procedure for the β-arylation with diaryliodonium salts General procedure: An 8mL vial was charged with Pd(OAc)2 (9.0mg, 0.1 equiv.), KTFA (122mg, 2.0 equiv.), Mesitylaryliodonium salt (0.4mmol), bis-sulfilimine ligand 9 (24mg, 0.1 equiv.), TFA (200μL), ketone (1.0mmol, 2.5 equiv.), H2O (100μL) and 1,4-dioxane (2mL). The vial was sealed with a PTFE lined cap (no inert atmosphere is required) and heated in a pie-block at 80°C for 12h under stirring. Then, the vial was allowed to cool to room temperature and the mixture was filtered through a small plug of silica gel, eluted with diethyl ether. The solvent was then removed in vacuo and flash column chromatography (hexane/ethyl acetate or DCM/methanol) of the residue gave the arylation product

Yield	Reaction Conditions	Operation in experiment
86 % de	Stage #1: 2,2-dimethyl-cyclohexanone With lithium chloride; lithium hexamethyldisilazane In tetrahydrofuran; 1,2-dimethoxyethane at 0℃; for 0.5h; Schlenk technique; Inert atmosphere; Stage #2: Acetic acid (1R,4S)-4-(tert-butyl-diphenyl-silanyloxy)-cyclopent-2-enyl ester With tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; (1R,2R)-1,2-bis[(2-diphenylphosphanyl)benzoylamino]cyclohexane In tetrahydrofuran; 1,2-dimethoxyethane at 20℃; for 0.5h; Schlenk technique; Inert atmosphere; Stage #3: In tetrahydrofuran; 1,2-dimethoxyethane at 0℃; for 22h; Schlenk technique; Inert atmosphere; Overall yield = 53 percent; Overall yield = 48.5 mg; diastereoselective reaction;
52 % de	Stage #1: 2,2-dimethyl-cyclohexanone With lithium diisopropyl amide In tetrahydrofuran at 0℃; for 0.5h; Schlenk technique; Inert atmosphere; Stage #2: Acetic acid (1R,4S)-4-(tert-butyl-diphenyl-silanyloxy)-cyclopent-2-enyl ester With tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; (R,R)-ANDEN-phenyl Trost Ligand In tetrahydrofuran at 20℃; for 0.5h; Schlenk technique; Inert atmosphere; Stage #3: In tetrahydrofuran at 0℃; for 2h; Schlenk technique; Inert atmosphere; Overall yield = 35 percent; diastereoselective reaction;