Org. Synth. 1951, 31, 104
DOI: 10.15227/orgsyn.031.0104
TETRAPHENYLETHYLENE
[Ethylene, tetraphenyl-]
Submitted by Robert E. Buckles and George M. Matlack
1.
Checked by T. L. Cairns and C. J. Albisetti.
1. Procedure
A solution of 75 g. (0.32 mole) of diphenyldichloromethane (Note 1) in 250 ml. of anhydrous benzene is placed in a 500-ml. round-bottomed flask fitted with a reflux condenser. To the solution is added 50 g. (0.78 g. atom) of powdered copper (Note 2). The mixture is boiled gently for 3 hours. The hot solution is filtered, and 250 ml. of absolute ethanol is added to the filtrate. On cooling 25–31 g. (47–60%) of light yellow crystals, m.p. 222–224°, are obtained. The mother liquor is concentrated to about 200 ml. by distillation from a 1-l. Claisen flask. Cooling the residue yields 6–12 g. of yellow product. Crystallization of this crude material from a 1:1 by volume mixture (12 ml. for each gram) of absolute ethanol and benzene gives an additional 2.5–10 g. of tetraphenylethylene, m.p. 223–224°. The total yield is 29–37 g. (55–70%).
2. Notes
1.
Diphenyldichloromethane is conveniently prepared from
benzophenone and
phosphorus pentachloride.
2 A product of b.p.
180–181°/17 mm. is obtained in about
90% yield.
2.
The checkers used bronze powder obtained from George Benda, Inc., Boonton, New Jersey. Some varieties of
copper powder tended to form a dense paste which did not disperse readily and resulted in lower yields.
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3. Discussion
This procedure is adapted from the method of Schlenk and Bergmann.
3 Tetraphenylethylene has been prepared by the reaction of
diphenylmethane with
diphenyldichloromethane;
4 by the reaction of
diphenyldichloromethane with
silver or
zinc;
4 by the reaction of
thiobenzophenone with
copper;
5 by the reaction of
diphenylmethane with
sulfur;
6 by the reduction of
benzophenone with
amalgamated zinc in the presence of
hydrochloric acid;
7 by the rearrangement of
1,2,2,2-tetraphenylethanol with
acetyl chloride;
8 by the reaction of
diphenylmethane with
bromine, followed by treatment of the product with
sodium iodide in
acetone;
9 by the reaction of
1,2-difluoro-1,2-diphenylethylene with
phenyllithium;
10 by the reaction of
diphenylchloromethane with
sodium or potassium amide in liquid
ammonia;
11 and by treatment of
2,2,3,3-tetraphenylpropionitrile with
potassium amide in liquid
ammonia.
12
Appendix
Chemical Abstracts Nomenclature (Collective Index Number);
(Registry Number)
amalgamated zinc
sodium or potassium amide
ethanol (64-17-5)
hydrochloric acid (7647-01-0)
ammonia (7664-41-7)
Benzene (71-43-2)
phosphorus pentachloride (10026-13-8)
acetyl chloride (75-36-5)
bromine (7726-95-6)
sulfur (7704-34-9)
copper,
copper powder (7440-50-8)
acetone (67-64-1)
Benzophenone (119-61-9)
zinc (7440-66-6)
diphenyldichloromethane (2051-90-3)
Diphenylmethane (101-81-5)
sodium iodide (7681-82-5)
Phenyllithium (591-51-5)
silver (7440-22-4)
Thiobenzophenone (1450-31-3)
potassium amide
Tetraphenylethylene,
Ethylene, tetraphenyl- (632-51-9)
1,2,2,2-tetraphenylethanol
1,2-difluoro-1,2-diphenylethylene
diphenylchloromethane (90-99-3)
2,2,3,3-tetraphenylpropionitrile
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