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1,2,3,4-Tetraphenylbutadiene

1,2,3,4-Tetraphenylbutadiene is an organic compound with the formula . It is a white solid.

The compound is prepared by reductive coupling of diphenylacetylene using lithium metal followed by hydrolysis of the resulting 1,4-dilithiobutadiene:

(Ph = C<sub>6</sub>H<sub>5</sub>)

1,4-Dilithiobutadiene is a precursor to several metallacycles by salt metathesis reactions:

(RM = PhP, PhAs, PhSb)

Structure

The isomer with mutually cis phenyl groups is common. According to X-ray crystallography, the phenyl groups are significantly rotated out of the plane of the 1,3-butadiene core.

Related compounds

1,1,4,4-Tetraphenylbutadiene is an isomer of 1,2,3,4-tetraphenylbutadiene with two phenyl group on each of the terminal carbon atoms of the diene. It has attracted some attention as an electroluminescent dye.

References