Adamantanylideneadamantane

Adamantanylideneadamantane [30541-56-1]

Name	Adamantanylideneadamantane
Synonyms
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
Molecular formula	C20H28
Molecular mass	268.45
SMILES code	C1(=C6C4CC5CC(C4)CC6C5)C2CC3CC(C2)CC1C3

TiCl4 / Zn / THF

; 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			CHCl3

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			CHCl3

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

0.1 mol

2-Adamantanone

Educts		Amount	Risk	Safety
2-Adamantanone		15.0 g	R no data	S 24/25
Reagents		Amount	Risk	Safety
Titanium tetrachloride	C	20.3 g	R 14-34	S 1/2-7/8-26-36/37/39-45
Zinc powder	F N	14.3 g	R 15-17-50/53	S 2-43-46-60-61
Solvents		Amount	Risk	Safety
Tetrahydrofuran	F Xi	430 mL	R 11-19-36/37	S 2-16-29-33
Cyclohexane	F Xn N	~250 mL	R 11-38-50/53-65-67	S 2-9-16-33-60-61-62
Ethanol	F		R 11	S 2-7-16
Others		Amount	Risk	Safety
Potassium carbonate	Xn	~21 g	R 22-36/37/38	S 22-26-37/39
Sodium sulfate	Xi	~5 g	R 36/37/38	S 26-36

0.1 mol

2-Adamantanone

Products		Amount	Risk	Safety
Adamantanylideneadamantane		11.4 g	R no data	S no data
Byproducts		Amount	Risk	Safety
2-Adamantanol			R no data	S 24/25

Waste	Disposal
evaporated solvent mixture	organic solvents, halogen free
aqueous phase after shaking out	solvent water mixtures, containing halogens
sodium sulfate	solid waste, free from mercury

0.1 mol

2-Adamantanone

	three-necked flask 1000 mL			heatable magnetic stirrer with magnetic stir bar
	internal thermometer			suction filter
	suction flask			bubble counter
	piston-operated pipette			protective gas piping
	addition funnel with pressure balance			separating funnel
	rotary evaporator			ice bath
	oil bath

0.1 mol

2-Adamantanone

Atom economy		48.3	%
Yield		85	%
Target product mass		11.4	g
Sum of input masses		430	g
Mass efficiency		26	mg/g
Mass index		38	g input / g product
E factor		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

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

IR: Adamantanylideneadamantane
[KBr, T%, cm-1]
[cm-1]	assignment
2966, 2916	aliph. C-H valence
2848	aliph. C-H valence

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