Toluene → Sumanene
Reaction equation
[C:1]([C:3]1[C:9](=O)[C:8](Cl)=[C:7](Cl)[C:5](=O)[C:4]=1[C:13]#N)#N.[C:15]1([CH3:21])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>>[CH2:1]1[C:8]2[CH:9]=[CH:3][C:4]3=[C:5]4[C:13]=2[C:4]2[C:5]5[C:16]6[C:17]4=[C:18]([CH:19]=[CH:20][C:15]=6[CH2:21][C:7]=5[CH:8]=[CH:9][C:3]1=2)[CH2:13]3Participants
Conditions
- Temperature
- 110 °C
Procedure
First, a double-necked flask of 10 mL was subjected to vacuum and dried by heat, and subsequently, its volume was displaced with argon. Next, a solution obtained by solving hexahydrosumanene (0.0 11 mmol, 3 mg) into 2 mL of toluene was added into the flask by using a syringe, and DDQ (0.0385 mmol, 9 mg) further was added therein, and subsequently, the system was heated at 110° C. for 20 hours. After the reaction, the solvent was evaporated under a reduced pressure, and residues were separated by thin layer chromatography (hexane), thereby obtaining Sumanene (yield: 2 mg, isolation yield: 67%) as an objective compound. Physical properties of this compound will be described below. In addition, UV-VIS absorption spectrograms of this compound will be shown in FIGS. 1 to 5. Used solvents are cyclohexylamine (CHA) in FIG. 1, tetrahydrofuran (THF) in FIG. 2, acetonitrile (CH3CN) in FIG. 3 and dichloromethane (CH2Cl2) in FIG. 4, where concentrations of all the solutions are 1.0×10−4 M. Moreover, FIG. 5 is a view showing all of the spectrograms of FIGS. 1 to 4 in one.
Workup
- customFirst, a double-necked flask of 10 mL was subjected to vacuum
- customdried
- temperatureby heat
- customNext, a solution obtained
- additionwas added into the flask
- customAfter the reaction
- customthe solvent was evaporated under a reduced pressure, and residues
- customwere separated by thin layer chromatography (hexane)
Sources & evidence
- ORD record
- ord-67f07cb5fa984536bd686f0a8220d384
- Source dataset
- uspto-grants-2008_10
- Patent number
- US07435859B2
Reaction notes
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