8817. Stilbene

Nomenclature

CAS number: 588-59-0
1,1′-(1,2-Ethenediyl)bis[benzene]; α,β-diphenylethylene; bibenzal; bibenzylidene.
C14H12; mol wt 180.25.
C 93.29%, H 6.71%.

Description and references

trans-Form prepd by Clemmensen reduction of benzoin: Shriner, Berger, Org. Synth. coll. vol. III, 786 (1955); cis-form by copper-chromite decarboxylation of α-phenylcinnamic acid: Buckles, Wheeler, ibid. coll. vol. IV, 857 (1963). Synthesis of cis- and trans-forms by the Wittig reaction and by decarboxylation of phenylcinnamic acids: Wheeler, Batlle de Pabon, J. Org. Chem. 30, 1473 (1965).

Chemical structure

Derivative

trans-Form.

Nomenclature

CAS number: 103-30-0

Properties

Crystals from 95% ethanol, mp 124°. bp760 306-307°. uv max (95% ethanol): 296, 305 nm (ε 28100; 26700). Volatile with steam. Practically insol in water. Sol in 90 parts cold alc, 13 parts boiling alc, freely in benzene, ether.

Derivative

cis-Form.

Nomenclature

CAS number: 645-49-8

Properties

Liquid, solidifies at 5°. bp10 135°; bp1.0 96°. nD25 1.6188. uv max (95% ethanol): 278 nm (ε 10200). Completely sol in cold abs alcohol.