Many syntheses have been developed.
 One popular route entails reduction of benzoin using zinc amalgam.

C₆H₅–CH(OH)–C(=O)–C₆H₅      trans-C₆H₅–CH=CH–C₆H₅
Both isomers of stilbene can be produced by decarboxylation of α-phenylcinnamic acid, trans-stilbene being produced from the (Z)-isomer of the acid.

Richard Heck and Tsutomu Mizoroki independently reported the synthesis of trans-stilbene by coupling of iodobenzene and styrene using a palladium(II) catalyst, in what is now known as the Mizoroki-Heck reaction.
 The Mizoroki approach produced the higher yield.

Stilbene undergoes reactions typical of alkenes.
 Trans-stilbene undergoes epoxidation with peroxymonophosphoric acid, H₃PO₅, producing a 74% yield of trans-stilbene oxide in dioxane.
 The epoxide product formed is a racemic mixture of the two enantiomers of 1,2-diphenyloxirane.
 The achiral meso compound (1R,2S)-1,2-diphenyloxirane arises from cis-stilbene, though peroxide epoxidations of the cis-isomer produce both cis- and trans-epoxide products.
 For example, using tert-butyl hydroperoxide, oxidation of cis-stilbene produces 0.8% cis-stilbene oxide, 13.5% trans-stilbene oxide, and 6.1% benzaldehyde.
 Enantiopure stilbene oxide has been prepared by Nobel laureate Karl Barry Sharpless.

Stilbene can be cleanly oxidised to benzaldehyde by ozonolysis or Lemieux–Johnson oxidation, and stronger oxidants such as acidified potassium permanganate will produce benzoic acid.
 Vicinal diols can be produced via the Upjohn dihydroxylation or enantioselectively using Sharpless asymmetric dihydroxylation with enantiomeric excesses as high as 100%.

Bromination of trans-stilbene produces predominantly meso-1,2-dibromo-1,2-diphenylethane (sometimes called meso-stilbene dibromide), in line with a mechanism involving a cyclic bromonium ion intermediate of a typical electrophilic bromine addition reaction; cis-stilbene yields a racemic mixture of the two enantiomers of 1,2-dibromo-1,2-diphenylethane in a non-polar solvent such as carbon tetrachloride, but the extent of production of the meso compound increases with solvent polarity, with a yield of 90% in nitromethane.
 The formation of small quantities of the two enantiomers of stilbene dibromide from the trans-isomer suggests that the bromonium ion intermediate exists in chemical equilibrium with a carbocation intermediate PhCHBr–C⁺(H)Ph with a vacant p orbital vulnerable to nucleophilic attack from either face.
The addition of bromide or tribromide salts restores much of the stereospecificity even in solvents with a dielectric constant above 35.

Upon UV irradiation it converts to cis-stilbene, a classic example of a photochemical reaction involving trans-cis isomerization, and can undergo further reaction to form phenanthrene.
Many syntheses have been developed.  One popular route entails reduction of benzoin using zinc amalgam.
C₆H₅–CH(OH)–C(=O)–C₆H₅      trans-C₆H₅–CH=CH–C₆H₅
Both isomers of stilbene can be produced by decarboxylation of α-phenylcinnamic acid, trans-stilbene being produced from the (Z)-isomer of the acid.
Richard Heck and Tsutomu Mizoroki independently reported the synthesis of trans-stilbene by coupling of iodobenzene and styrene using a palladium(II) catalyst, in what is now known as the Mizoroki-Heck reaction.  The Mizoroki approach produced the higher yield.
Stilbene undergoes reactions typical of alkenes.  Trans-stilbene undergoes epoxidation with peroxymonophosphoric acid, H₃PO₅, producing a 74% yield of trans-stilbene oxide in dioxane.  The epoxide product formed is a racemic mixture of the two enantiomers of 1,2-diphenyloxirane.  The achiral meso compound (1R,2S)-1,2-diphenyloxirane arises from cis-stilbene, though peroxide epoxidations of the cis-isomer produce both cis- and trans-epoxide products.  For example, using tert-butyl hydroperoxide, oxidation of cis-stilbene produces 0.8% cis-stilbene oxide, 13.5% trans-stilbene oxide, and 6.1% benzaldehyde.  Enantiopure stilbene oxide has been prepared by Nobel laureate Karl Barry Sharpless.
Stilbene can be cleanly oxidised to benzaldehyde by ozonolysis or Lemieux–Johnson oxidation, and stronger oxidants such as acidified potassium permanganate will produce benzoic acid.  Vicinal diols can be produced via the Upjohn dihydroxylation or enantioselectively using Sharpless asymmetric dihydroxylation with enantiomeric excesses as high as 100%.
Bromination of trans-stilbene produces predominantly meso-1,2-dibromo-1,2-diphenylethane (sometimes called meso-stilbene dibromide), in line with a mechanism involving a cyclic bromonium ion intermediate of a typical electrophilic bromine addition reaction; cis-stilbene yields a racemic mixture of the two enantiomers of 1,2-dibromo-1,2-diphenylethane in a non-polar solvent such as carbon tetrachloride, but the extent of production of the meso compound increases with solvent polarity, with a yield of 90% in nitromethane.  The formation of small quantities of the two enantiomers of stilbene dibromide from the trans-isomer suggests that the bromonium ion intermediate exists in chemical equilibrium with a carbocation intermediate PhCHBr–C⁺(H)Ph with a vacant p orbital vulnerable to nucleophilic attack from either face. The addition of bromide or tribromide salts restores much of the stereospecificity even in solvents with a dielectric constant above 35.
Upon UV irradiation it converts to cis-stilbene, a classic example of a photochemical reaction involving trans-cis isomerization, and can undergo further reaction to form phenanthrene.
(E)-Stilbene