Adamantanylideneadamantane [30541-56-1]
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Name | Adamantanylideneadamantane |
Synonyms |
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Name in Chemical Abstracts | Tricyclo[3.3.1.1(3,7)]decane, tricyclo[3.3.1.1(3,7)]decylidene- |
CAS No | 30541-56-1 |
EINECS No |
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Molecular formula | C20H28 |
Molecular mass | 268.45 |
SMILES code | C1(=C6C4CC5CC(C4)CC6C5)C2CC3CC(C2)CC1C3 |
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TiCl4 / Zn / THF |
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; Side reactions |
1H-NMR
1H-NMR: crude product |
500 MHz, CDCl3 |
delta [ppm] | mult. | atoms | assignment |
1.63-1.69 | m | 8 H | CH2 |
1.79-1.86 | m | 12 H | CH2 |
1.90 | m | 4 H | 5-H, 5'-H, 7-H, 7'-H |
2.88 | m | 4 H | 1-H, 1'-H, 3-H, 3'-H |
7.26 |
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| CHCl3 |
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1H-NMR: Adamantanylideneadamantane |
500 MHz, CDCl3 |
delta [ppm] | mult. | atoms | assignment |
1.63-1.69 | m | 8 H | CH2 |
1.79-1.86 | m | 12 H | CH2 |
1.90 | m | 4 H | 5-H, 5'-H, 7-H, 7'-H |
2.88 | m | 4 H | 1-H, 1'-H, 3-H, 3'-H |
7.26 |
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| CHCl3 |
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Synthesis of adamantylideneadamantane from adamantanone
Reaction type: |
McMurry reaction, reductive coupling, alkenesynthesis |
Substance classes: |
ketone, alkene |
Techniques: |
working with cover gas, adding dropwise with a piston-operated
pipette, adding dropwise with an addition funnel, stirring with magnetic
stir bar, heating under reflux, shaking out, extracting, Abfiltrieren,
evaporating with rotary evaporator, recrystallizing, use of an ice
cooling bath, heating with oil bath |
Degree of difficulty: |
Difficult |
http://kriemhild.uft.uni-bremen.de/nop/en/instructions/pdf/3012_en.pdf
Operating scheme
Educts |
|
Amount |
Risk |
Safety |
2-Adamantanone |
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15.0 g |
R no data
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S 24/25
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Reagents |
|
Amount |
Risk |
Safety |
Titanium tetrachloride |
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C |
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20.3 g |
R 14-34
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S 1/2-7/8-26-36/37/39-45
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Zinc powder |
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F |
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N |
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14.3 g |
R 15-17-50/53
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S 2-43-46-60-61
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Solvents |
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Amount |
Risk |
Safety |
Tetrahydrofuran |
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F |
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Xi |
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430 mL |
R 11-19-36/37
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S 2-16-29-33
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Cyclohexane |
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~250 mL |
R 11-38-50/53-65-67
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S 2-9-16-33-60-61-62
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Ethanol |
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F |
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R 11
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S 2-7-16
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Others |
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Amount |
Risk |
Safety |
Potassium carbonate |
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Xn |
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~21 g |
R 22-36/37/38
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S 22-26-37/39
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Sodium sulfate |
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Xi |
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~5 g |
R 36/37/38
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S 26-36 |
Products |
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Amount |
Risk |
Safety |
Adamantanylideneadamantane |
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11.4 g |
R no data
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S no data
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Byproducts |
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Amount |
Risk |
Safety |
2-Adamantanol |
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R no data
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S 24/25
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Waste |
Disposal |
evaporated solvent mixture
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organic solvents, halogen free
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aqueous phase after shaking out
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solvent water mixtures, containing halogens
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sodium sulfate
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solid waste, free from mercury
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three-necked flask 1000 mL |
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heatable magnetic stirrer with magnetic stir bar |
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internal thermometer |
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suction filter |
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suction flask |
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bubble counter |
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piston-operated pipette |
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protective gas piping |
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addition funnel with pressure balance |
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separating funnel |
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rotary evaporator |
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ice bath |
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oil bath |
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Atom economy |
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48.3 |
% |
Yield |
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85 |
% |
Target product mass |
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11.4 |
g |
Sum of input masses |
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430 |
g |
Mass efficiency |
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26 |
mg/g |
Mass index |
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38 |
g input / g product |
E factor |
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37 |
g waste / g product |
Chromatogram
GC: crude product |
column | SE-54, L= 25 m, ID 0.32 mm, DF 0.25 µm (Macherey & Nagel) |
inlet | Gerstel KAS, injector: 250°C, split injection 1:20, 0.1 µL |
carrier gas | N2, pre-column pressure 62 kPa, 1.04 mL/min |
oven | 100 °C (1 min), 10 °C/min --> 250 °C (30 min) |
detector | FID, 275 °C |
integration | percent concentration calculated from relative peak area |
GC: pure product |
column | SE-54, L= 25 m, ID 0.32 mm, DF 0.25 µm (Macherey & Nagel) |
inlet | Gerstel KAS, injector: 250°C, split injection 1:20, 0.1 µL |
carrier gas | N2, pre-column pressure 62 kPa, 1.04 mL/min |
oven | 100 °C (1 min), 10 °C/min --> 250 °C (30 min) |
detector | FID, 275 °C |
integration | percent concentration calculated from relative peak area |
13C-NMR
13C-NMR: crude product |
125 MHz, CDCl3 |
delta [ppm] | assignment |
28.6 | C5, C5', C7, C7' |
31.9 | C1, C1', C-3, C3' |
37.3 | C6, C6' |
39.6 | C4, C4', C8, C8', C9, C9', C10, C10' |
133.1 | C2, C2' |
76.5-77.5 | CDCl3 |
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13C-NMR: Adamantanylideneadamantane |
125 MHz, CDCl3 |
delta [ppm] | assignment |
28.6 | C5, C5', C7, C7' |
31.9 | C1, C1', C-3, C3' |
37.3 | C6, C6' |
39.6 | C4, C4', C8, C8', C9, C9', C10, C10' |
133.1 | C2, C2' |
76.5-77.5 | CDCl3 |
IR
IR: crude product |
[KBr, T%, cm-1] |
[cm-1] | assignment |
2966, 2916 | aliph. C-H valence |
2848 | aliph. C-H valence |
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IR: Adamantanylideneadamantane |
[KBr, T%, cm-1] |
[cm-1] | assignment |
2966, 2916 | aliph. C-H valence |
2848 | aliph. C-H valence |
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