1,1-Diphenylethylene

Chemical Properties

Clear colorless to golden liquid

Uses

1,1-Diphenylethylene is used in the preparation of 2-chloro-1,1-diphenyl-ethene by reacting with benzeneseleninyl chloride and aluminum(III) chloride as reagents. It acts as an intermediate in organic synthesis as well as in pharmaceuticals.

Synthesis Reference(s)

The Journal of Organic Chemistry, 26, p. 4199, 1961 DOI: 10.1021/jo01069a005

Reactivity Profile

1,1-Diphenylethylene (DPE) is well known for its inability to undergo homopolymerization but can participate in radical copolymerizations. The participation of DPE in radical polymerization leads to the formation of stable DPE radicals by resonance stabilization of the radical by the two phenyl groups and a strong steric hindrance for the addition of any other monomer. Thus, DPE has drastic effects on radical polymerizati[1].

Synthesis

1,1-Diphenylethylene can be prepared by the action of alcoholic potassium hydroxide on unsymmetrical diphenylchloroethane; by the action of aluminum chloride on benzene and tribromoethylene; and by dehydration of the carbinol which can be prepared by the action of methylmagnesium iodide on benzophenone, or phenylmagnesium bromide on acetophenone or ethyl acetate.

References

[1] Sophie Viala . “Structural control in radical polymerization with 1,1-diphenylethylene. 1. Copolymerization of 1,1-diphenylethylene with methyl methacrylate.” Polymer 43 26 (2002): Pages 7231-7241.