| 94% |
With pyridine; titanium tetrachloride; zinc In 1,4-dioxane for 0.0833333h; microwave irradiation; |
|
| 92% |
With titanium(III) chloride; zinc In 1,2-dimethoxyethane for 2h; Heating; |
|
| 92% |
With woollins’ reagent In toluene for 20h; Heating; |
|
| 92% |
With titanium(III) chloride; zinc In 1,2-dimethoxyethane for 2h; Inert atmosphere; Reflux; regioselective reaction; |
|
| 90% |
With titanium tetrachloride; zinc In tetrahydrofuran Heating; |
|
| 84% |
With Lawessons reagent at 152℃; for 0.045h; Microwave irradiation; |
|
| 65% |
With titanium tetrachloride; zinc In tetrahydrofuran for 10h; Inert atmosphere; Reflux; |
1
To the suspension of Zn (29 g, 443 mol) in dry THF (100 mL) was added TiCl4 (24 mL, 219 mmol) was added under N2 at 0 °C. Then, the mixture was refluxed for 2 h. To the mixture was added the 40 mL THF solution of fluorenone (10 g, 55.4 mmol) via cannula. After being refluxed for 10 h, the reaction was quenched with saturated aqueous solution of NH4Cl at 0 °C. The organic products were extracted with ethyl acetate. The organic layer was washed with water and brine. The organic layer was dried over anhydrous Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by silica-gel chromatography (hexane/CH2 Cl2 = 95/5 to 9/1) to give the desired product 1 as a red solid (5.91 g, 18.0 mmol, 65% yield). The product was confirmed by comparison with the reported 1H NMR chemical shifts. |
| 64% |
With titanium tetrachloride; triethylamine In dichloromethane |
|
| 62% |
With titanium tetrachloride; zinc In tetrahydrofuran for 5h; Inert atmosphere; Schlenk technique; Reflux; |
|
| 46.1% |
With Lawessons reagent In toluene Reflux; |
|
| 44% |
With TiCl2*2THF In tetrahydrofuran for 24h; Heating; |
|
|
With diethyl ether; acetyl chloride; zinc |
|
|
Multi-step reaction with 2 steps
1: boron trifluoride etherate / CHCl3 / 3 h / Heating
2: 93 percent / W(CO)6 / chlorobenzene / 24 h / 160 °C |
|
|
Multi-step reaction with 2 steps
1: sodium methylate; methanol
2: KI; glacial acetic acid |
|
|
Multi-step reaction with 2 steps
1: PCl5
2: alcoholic K2S solution |
|
|
Multi-step reaction with 2 steps
1: PCl5 / 160 °C
2: copper powder; benzene |
|
|
Multi-step reaction with 2 steps
1: 100 °C
2: hydrochloric acid; glacial acetic acid |
|
|
Multi-step reaction with 2 steps
1: ethanolic solution / <0 / Einleiten von H2S und HCl und weiteres Einleiten von H2S
2: copper-powder; xylene |
|
|
With titanium tetrachloride; triethylamine In dichloromethane; chloroform at 0 - 25℃; for 5h; Inert atmosphere; |
4
Example 4: Synthesis of bifluorenylidene (BFD); 10 ml of anhydrous trichloromethane and 4.16 ml of triethylamine (30 nmol) are mixed under N2 atmosphere at 00C. 20 ml of a IM solution of titanium tetrachloride in dichloromethane (20 mmol) are added under nitrogen at 00C. The reaction is stirred for Ih at 00C and to this reaction mixture 1.800 g of fluorenone are added (10 mmol) and the stirring is continued for further 5 hours at 0-250C. The reaction mixture is then quenched with a saturated solution of NH4Cl (20 ml). The organic layer is separated and the aqueous layer is extracted with CH2C1.3 (3 x 30 ml). The pooled organic extracts are washed with brine (20 ml) and dried on anhydrous Na2SO4. The solvent is removed and the residue is chromatographed on a silica gel column. |
|
With tributylphosphine |
|
|
Multi-step reaction with 3 steps
1.1: hydrogen sulfide; hydrogenchloride / ethanol / 0 - 5 °C
2.1: tetrahydrofuran; diethyl ether
2.2: 0.17 h / 0 °C
3.1: tetrabutyl ammonium fluoride / tetrahydrofuran; diethyl ether / 20 °C |
|
|
Multi-step reaction with 2 steps
1: hydrazine hydrate / ethanol / 6 h / Inert atmosphere; Reflux
2: 1,3-bis-(diphenylphosphino)propane; trans-chloro(1-naphthyl)bis-(triphenylphosphine)nickel(II); potassium <i>tert</i>-butylate / 1,4-dioxane / 110 °C / Inert atmosphere |
|
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