52 Works

Short-RInChIKey=SA-FUHFF-UHFFFADPSC-MVJGJYRFWK-UHFFFADPSC-NUHFF-NUHFF-NUHFF-ZZZ

Simone Gräßle
1H-Indole (250 mg, 2.1 mmol, 1.00 equiv) was dissolved in 10 mL of abs. methylene chloride (N2 atmosphere) and dimethylalumanylium;chloride in hexane (1 M, 2.56 mL, 2.6 mmol, 1.20 equiv) was added at 0 °C. The reaction was stirred for 15 min at 0 °C and 2-phenylacetyl chloride (330 mg, 282 μL, 2.13 mmol, 1.00 equiv) was added. The reaction was allowed to come to room temperature and was stirred at 21 °C for 14...

Short-RInChIKey=SA-FUHFF-UHFFFADPSC-AXGWEHWIGI-UHFFFADPSC-NUHFF-NUHFF-NUHFF-ZZZ

Robin Bär
A 1 M thiophenol solution in diethyl ether (165 mg, 1.50 mL, 1.5 mmol, 2.87 equiv) was added to the propellane solution (1.00 mL) and the mixture was stirred for 15 min at 21 °C. The solution was diluted with 10 mL of pentane and was washed with 10 mL of a 1 M NaOH solution. The organic layer was dried by the addition of Na2SO4. The mixture was filtered through a glass funnel and...

Short-RInChIKey=SA-FUHFF-UHFFFADPSC-XHEOXSQMBW-UHFFFADPSC-NUHFF-NUHFF-NUHFF-ZZZ

Nicole Jung & Simone Gräßle
To a flame-dried 250 mL round-bottemed flask containing crude 1-acetoxy-1,2-benziodoxol-3-(1H)-one (10.6 g, 36 mmol, 1.00 equiv) was added anhydrous cesium;fluoride (138 mg, 910 μmol, 0.0250 equiv), anhydrous acetonitrile (77.0 mL) and trimethyl(trifluoromethyl)silane (7.25 g, 7.53 mL, 51 mmol, 1.40 equiv) successively under inert atmosphere. The reaction mixture was stirred vigorously for 24 h. The white solid suspended in the reaction mixture was then isolated by filtration. This solid was dissolved in 135 mL of chloroform...

Short-RInChIKey=SA-FUHFF-UHFFFADPSC-XLGLVRGMYS-UHFFFADPSC-NUHFF-NWPAI-NUHFF-ZZZ

Nicolai Wippert
A mixture of ethyl 5-amino-1H-pyrazole-4-carboxylate (1.00 g, 6.5 mmol, 1.00 equiv) in conc. hydrochloric acid (940 mg, 2.15 mL, 26 mmol, 3.99 equiv) and 3 mL of water was cooled to 0 °C and a solution of sodium nitrite (667 mg, 9.7 mmol, 1.50 equiv) in 10 mL of water was added. After stirring for 30 min, a mixture of diisopropylamine (848 mg, 1.17 mL, 8.4 mmol, 1.30 equiv) and potassium carbonate (1.78 g, 13...

Short-RInChIKey=SA-FUHFF-UHFFFADPSC-AMOBBDHYJV-UHFFFADPSC-NUHFF-NUHFF-NUHFF-ZZZ

Steven Susanto
Methyl 2-(bromomethyl)prop-2-enoate (16.0 g, 89 mmol, 1.00 equiv) was dissolved in 200 mL of THF and 200 mL of dest. water. Ethanethioic S-acid (10.2 g, 9.54 mL, 134 mmol, 1.50 equiv) was added and the mixture was cooled to 0 °C. Disodium carbonate (14.2 g, 134 mmol, 1.50 equiv) was added and the resulting mixture was stirred at 21 °C for 2 h. After disappearance of the starting material (TLC control) the reaction was diluted...

Short-RInChIKey=SA-FUHFF-UHFFFADPSC-IPOJHZYBCZ-UHFFFADPSC-NUHFF-NUHFF-NUHFF-ZZZ

Robin Bär
The propellane solution (1.00 mL, 0.40 M in Et2O, 400 μmol, 2.00 equiv) was added to a solution of the 1,3-dichloro-5-[(3,5-dichlorophenyl)disulfanyl]benzene (71.2 mg, 200 μmol, 1.00 equiv) in 1.00 mL of THF under argon atmosphere and the mixture was irradiated with UV light (500 W) for 20 min. After evaporation of the solvent under reduced pressure, the crude residue was purified via column chromatography.

Short-RInChIKey=SA-FUHFF-UHFFFADPSC-MRDPMFJFXN-UHFFFADPSC-NUHFF-NUHFF-NUHFF-ZZZ

Robin Bär & Martin Nieger
The propellane solution (28.9 mg, 1.00 mL, 437 μmol, 1.00 equiv) was added to a solution of (phenyldisulfanyl)benzene (143 mg, 655 μmol, 1.50 equiv) and 1-methoxy-4-[(4-methoxyphenyl)disulfanyl]benzene (182 mg, 655 μmol, 1.50 equiv) in THF (1.00 mL) under argon atmosphere and the mixture was irradiated with UV light (500 W) for 20 min. After evaporation of the solvent under reduced pressure, the crude residue was purified via column chromatography and preparative TLC.

Short-RInChIKey=SA-FUHFF-UHFFFADPSC-ILVXOBCQQY-UHFFFADPSC-NUHFF-NUHFF-NUHFF-ZZZ

Hannes Kühner
To a stirred solution of pyridine (1.47 g, 1.50 mL, 19 mmol, 1.00 equiv) in chloroform (9.00 mL) was added 70% 3-chlorobenzenecarboperoxoic acid (4.59 g, 19 mmol, 1.00 equiv), portionwise at 0 °C. The resulting mixture was stirred at room temperature for 12 h, at which time complete consumption of starting material was observed by TLC. The reaction mixture was diluted with chloroform, and solid potassium carbonate (10,3 g, 75 mmol, 4,0 equiv) was added....

Short-RInChIKey=SA-FUHFF-UHFFFADPSC-RJKOTIRDIV-UHFFFADPSC-NUHFF-NUHFF-NUHFF-ZZZ

Robin Bär
The propellane solution (1.00 mL, 0.40 M in Et2O, 400 μmol, 2.00 equiv) was added to a solution of the 1-methyl-4-[(4-methylphenyl)disulfanyl]benzene (49.3 mg, 200 μmol, 1.00 equiv) in 1.00 mL of THF under argon atmosphere and the mixture was irradiated with UV light (500 W) for 20 min. After evaporation of the solvent under reduced pressure, the crude residue was purified via column chromatography.

Short-RInChIKey=SA-FUHFF-UHFFFADPSC-AWYXHOMVLA-UHFFFADPSC-NUHFF-NUHFF-NUHFF-ZZZ

Robin Bär
The propellane solution (1.00 mL, 0.52 M in Et2O, 522 μmol, 1.00 equiv) was added to a solution of the 1-methoxy-4-[(4-methoxyphenyl)disulfanyl]benzene (436 mg, 1.6 mmol, 3.00 equiv) in 1.00 mL of THF under argon atmosphere and the mixture was irradiated with UV light (500 W) for 20 min. After evaporation of the solvent under reduced pressure, the crude residue was purified via column chromatography.

Short-RInChIKey=SA-FUHFF-UHFFFADPSC-GCSMQZIBGL-UHFFFADPSC-NUHFF-NUHFF-NUHFF-ZZZ

Alex Braun
In a vial, iodophenylhydrazine (0.500 g, 1.92 mmol, 1.00 equiv.) and methyl-2-butanone (0.41 mL, 0.331 g, 3.85 mmol, 2.00 equiv.) were dissolved in 7.0 mL of EtOH. After addition of 0.10 mL conc. H2SO4 the mixture was stirred for 12 h at 80 °C. After cooling down, 20 mL of H2O was added to the crude reaction mixture and the product was extracted with 3 × 25 mL of dichloromethane. The combined organic phases were...

Short-RInChIKey=SA-FUHFF-UHFFFADPSC-UWRWLWRXCL-UHFFFADPSC-NUHFF-NBSLK-NUHFF-ZZZ

Claudine Herlan
Under inert conditions, 4-trimethylsilylethinylazobenzene (340 mg, 1.00 mmol, 1.00 equiv.) was dissolved in 15 mL of dry methanol. After addition of potassium carbonate (163 mg, 1.18 mmol, 1.30 equiv.), the mixture was stirred for 24 h at 21 °C. The precipitated solid was filtered off, washed with water and dried under reduced pressure. The product was obtained as an orange-brown solid in 99% yield (207 mg, 0.900 mmol).

Short-RInChIKey=SA-FUHFF-UHFFFADPSC-WKODVHZBYI-UHFFFADPSC-NUHFF-NICYD-NUHFF-ZZZ

Claudine Herlan
Aminophenol (2.20 g, 20.1 mmol, 1.00 equiv.) was dissolved in 8.50 mL of 5 M HCl (50.0 mmol, 2.50 equiv.) and stirred for 45 min at 21 °C. After cooling to 0–5 °C, sodium nitrite (1.39 g, 20.1 mmol, 1.00 equiv.) was dissolved in 9.00 mL water and added dropwise to the reaction. After 2 h, phenol (1.52 g, 16.1 mmol, 0.800 equiv.) was dissolved in 18.5 mL of 2 M NaOH and was added...

Short-RInChIKey=SA-FUHFF-UHFFFADPSC-JODUWSZJDO-UHFFFADPSC-NUHFF-NGHTP-NUHFF-ZZZ

Claudine Herlan
Under inert conditions, azophenole (500 mg, 2.33 mmol, 1.00 equiv.) and potassium carbonate (1.60 g, 11.6 mmol, 5.00 equiv.) were dissolved in 30 mL of dry acetone und stirred for 30 min at 21 °C. After addition of propargylbromide (1.67 g, 14.0 mmol, 6.00 equiv.), the mixture was stirred for another 24 h at 21 °C. The solvent was removed under reduced pressure.

Short-RInChIKey=SA-FUHFF-UHFFFADPSC-ZRNYVIIOMH-UHFFFADPSC-NUHFF-NWIMK-NUHFF-ZZZ

Claudine Herlan
4-Bromoazobenzene (510 mg, 1.50 mmol, 1.00 equiv.), copper(I)-iodide (28.5 mg, 0.150 mmol, 0.100 equiv.), triphenylphosphine (63.0 mg, 0.240 mmol, 0.160 equiv.) and tris(dibenzylideneacetone)-dipalladium(0) (27.5 mg, 0.0300 mmol, 0.0200 equiv.) were mixed and degassed. After addition of 10 mL of dry trimethylamine, the reaction was stirred for 10 min. Trimethylsilylacetylene (368 mg, 3.75 mmol, 2.50 equiv.) was added and the reaction was stirred for 5 days at 90 °C. The solvent was removed and the residue...

Short-RInChIKey=SA-FUHFF-UHFFFADPSC-OYBOVXXFJY-UHFFFADPSC-NUHFF-NUHFF-NUHFF-ZZZ

Claudine Herlan
3-Chloropropylamine hydrochloride (6.00 g, 46.0 mmol, 1.00 equiv) was dissolved in 100 mL of water. Sodium azide (9.00 g, 138 mmol, 3.00 equiv) was added and the mixture was stirred for 18 h at 21 °C. The solvent was reduced to 2/3 of its volume. The remaining mixture was cooled to 0 °C and 100 mL diethylether were added. Potassium hydroxide (6.00 g, 107 mmol, 2.30 equiv.) was added in portions and the organic layer...

Short-RInChIKey=SA-FUHFF-UHFFFADPSC-KPGPIQKEKA-UHFFFADPSC-NUHFF-NUHFF-NUHFF-ZZZ

Jérôme Klein
In a 100 mL pear-shaped flask, phosphoryl chloride (46.4 mL, 496.8 mmol, 60 eq), was added to 3-phenylquinoxalin-2(1H)-one (1840 mg, 8.3 mmol, 1 eq) and heated to 100 °C for 2 h. The reaction was cooled to 21 °C and poured on ice and rested for overnight. The remaining aqueous layer was extracted with DCM (3x) and the organic layers were combined, dried over Na2SO4 and concentrated under reduced pressure.

Short-RInChIKey=SA-FUHFF-UHFFFADPSC-USTASXYEIS-UHFFFADPSC-NUHFF-NUHFF-NUHFF-ZZZ

Robin Bär
The propellane solution (1.00 mL, 0.437 M in Et2O, 437 μmol, 1.00 equiv) was added to a solution of (phenyldisulfanyl)benzene(143 mg, 655 μmol, 1.50 equiv) and 1-methyl-4-[(4-methylphenyl)disulfanyl]benzene (161 mg, 655 μmol, 1.50 equiv) in THF (1.00 mL) under argon atmosphere and the mixture was irradiated with UV light (500 W) for 20 min. After evaporation of the solvent under reduced pressure, the crude residue was purified via column chromatography.

Short-RInChIKey=SA-FUHFF-UHFFFADPSC-GXKYJSRHQM-UHFFFADPSC-NUHFF-NUHFF-NUHFF-ZZZ

Robin Bär
The propellane solution (1.00 mL, 0.437 M in Et2O, 437 μmol, 1.00 equiv) was added to a solution of (benzyldisulfanyl)methylbenzene (323 mg, 1.3 mmol, 3.00 equiv) in THF (1.00 mL) under argon atmosphere and the mixture was irradiated with UV light (500 W) for 20 min. After evaporation of the solvent under reduced pressure, the crude residue was purified via HPLC.

Short-RInChIKey=SA-FUHFF-UHFFFADPSC-OUWLZEOAVC-UHFFFADPSC-NUHFF-NUHFF-NUHFF-ZZZ

Alex Braun
A mixture of (4-bromophenyl)hydrazine;hydrochloride (2.00 g, 8.95 mmol, 1.00 equiv.), 3-methyl-2-butanone (2.14 mL, 20.1 mmol, 2.25 equiv.) and 0.46 mL of conc. H2SO4 was dissolved in 32.5 mL of ethanol, heated to 80 °C and stirred for 6 h. After cooling of the reaction mixture to room temperature, the crude product was extracted with dichloromethane. The combined organic phases were washed with NaHCO3 solution and water, dried over Na2SO4 and the solvent was removed under...

Short-RInChIKey=SA-FUHFF-UHFFFADPSC-JKPTZWVDCS-UHFFFADPSC-NUHFF-NUHFF-NUHFF-ZZZ

Robin Bär
1-Iodo-2-phenylbenzene (1.27 g, 4.5 mmol, 1.00 equiv), copper(I) iodide (86.4 mg, 453 μmol, 0.100 equiv), sulfur (145 mg, 4.5 mmol, 1.00 equiv) and sodium sulfide nonahydrate (1.09 g, 4.5 mmol, 1.00 equiv) were mixed in a vial under argon atmosphere. N,N-dimethylformamide (8.50 mL) was added and the reaction mixture was heated at 100 °C for 16 h. The reaction was quenched by the addition of 1 mL of H2O. The aqueous layer was extracted with...

Short-RInChIKey=SA-FUHFF-UHFFFADPSC-QZRDVUOPVS-UHFFFADPSC-NUHFF-NUHFF-NUHFF-ZZZ

Simone Gräßle & Jérôme Klein
2-Azido-3-phenylquinoxaline, Potassium iodine and Sodium azide were dissolved in DMF and heated to reflux until TLC shows the end of reaction (3h). Ethyl acetate and dist water were then added. The organic layer was then washed with brine (3x). The organic layer was then dried over Na2SO4 and the solvent was then removed. The product was purified with chromatography column chromatography (1:10 EtOAc/Cyclohexane) to afford a yellowish solid.

Short-RInChIKey=SA-FUHFF-UHFFFADPSC-QFUYDAGNUJ-UHFFFADPSC-NUHFF-NUHFF-NUHFF-ZZZ

Robin Bär
Tert-butyl nitrite (1.83 g, 2.11 mL, 18 mmol, 3.00 equiv) was added to a solution of para-toluenesulfonic acid monohydrate (3.37 g, 18 mmol, 3.00 equiv) in acetonitrile (25.0 mL), followed by 2-phenylaniline (1.00 g, 5.9 mmol, 1.00 equiv). After consumption of the starting material, potassium iodide (4.90 g, 30 mmol, 5.00 equiv), dissolved in 5 mL water, was added slowly and the mixture was stirred for 2 h at 21 °C. The product was extracted...

Short-RInChIKey=SA-FUHFF-UHFFFADPSC-MRDPMFJFXN-UHFFFADPSC-NUHFF-NUHFF-NUHFF-ZZZ

Robin Bär
The propellane solution (1.00 mL, 0.44 M in Et2O, 437 μmol, 1.00 equiv) was added to a solution of (phenyldisulfanyl)benzene (143 mg, 655 μmol, 1.50 equiv) and 1-methoxy-4-[(4-methoxyphenyl)disulfanyl]benzene (182 mg, 655 μmol, 1.50 equiv) in THF (1.00 mL) under argon atmosphere and the mixture was irradiated with UV light (500 W) for 20 min. After evaporation of the solvent under reduced pressure, the crude residue was purified via column chromatography and preparative TLC.

Short-RInChIKey=SA-FUHFF-UHFFFADPSC-UCPMQTTXXM-UHFFFADPSC-NUHFF-NRHPV-NUHFF-ZZZ

Nicolai Wippert
To a mixture of 5-amino-1H-pyrazole-4-carbonitrile (2.00 g, 19 mmol, 1.00 equiv) in 6 mL of water, conc. hydrochloric acid (6.17 mL, 74 mmol, 4.00 equiv) was added. The mixture was cooled to 0 °C and a solution of sodium;nitrite (1.91 g, 28 mmol, 1.50 equiv) in 20 mL of water was added. Additional 10 mL of water were added to get to slurry able to be stirred. After stirring for 30 min at 0 °C,...

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  • Karlsruher Institut für Technologie - Institut für Organische Chemie
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