42788-50-1

Basic information

• Product Name: (Z)-Stilbene-α,β-diol
• Synonyms: (Z)-1,2-Diphenyl-1,2-ethenediol;(Z)-Stilbene-α,β-diol
• CAS NO: 42788-50-1
• Molecular Formula: C14H12O2
• Molecular Weight: 0
• Mol File: 42788-50-1.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (Z)-Stilbene-α,β-diol(CAS DataBase Reference)
• NIST Chemistry Reference: (Z)-Stilbene-α,β-diol(42788-50-1)
• EPA Substance Registry System: (Z)-Stilbene-α,β-diol(42788-50-1)

Safety Data

• Hazardous Substances Data: 42788-50-1(Hazardous Substances Data)

Upstream product

• 103-30-0 (E)-1,2-diphenyl-ethene 
• 75-09-2 dichloromethane 
• 7529-22-8 4-methylmorpholine N-oxide 
• 134-81-6 benzil 

Downstream Products

• 21324-77-6 (4,5-diphenyl-oxazol-2-yl)-cyanamide 

Relevant articles and documents

Facilitation of turnover in the ADH by additives which catalyze the hydrolysis of the OS(VI) glycolate esters

Osmium-catalyzed methods of addition to an olefin are discussed. In the method of asymmetric dihydroxylation of the present invention, an olefin, a chiral ligand, an organic solvent, water, an oxidant, an osmium-containing compound and an organic soluble anion are combined. The presence of the organic soluble anion allows the asymmetric dihydroxylation reaction to occur rapidly and the amount of olefin that is diydroxylated is high with concomitantly less chiral ligand and osmium-containing catalyst than previously achieved.

Ligands for ADH: cinchona alkaloids and moderately sized organic substituents linked through a planar aromatic spacer group

Osmium-catalyzed methods of addition to an olefin are discussed. In the method of asymmetric dihydroxylation of the present invention, an olefin, a chiral ligand, an organic solvent, an aqueous solution, a base, a ferricyanide salt and an osmium-containing compound are combined. The chiral ligand is an alkaloid or alkaloid derivative linked to an organic substituent of at least 300 daltons molecular weight through a planar aromatic spacer group. The organic substituent can be another alkaloid or alkaloid derivative. With the described chiral ligands, asymmetric dihydroxylation of olefins with high yields and enantiomeric excesses are achieved.

Methods for catalytic asymmetric dihydroxylation of olefins

Osmium-catalyzed methods of addition to an olefin are discussed. In the method of asymmetric dihydroxylation of the present invention, an olefin, a chiral ligand, an organic solvent, water, an oxidant and an osmium-containing compound are combined. In the method of asymmetric oxyamination of the present invention, an olefin, a chiral ligand, an organic solvent, water, a metallo-chloramine derivative, an osmium-containing compound and, optionally, a tetraalkyl ammonium compound are combined. In the method of asymmetric diamination of the present invention, an olefin, a chiral ligand, an organic solvent, a metallo-chloramine derivative, an amine and an osmium-containing compound are combined. In one embodiment, an olefin, a chiral ligand which is a polymeric dihydroquinidine derivative or a dihydroquinine derivative, acetone, water, a base, an oxidant and osmium tetroxide are combined to effect asymmetric dihydroxylation of the olefin.

Reduction of Unsymmetrical Benzils Using Sodium Dithionite

Contrary to a previous report, reduction of unsymmetrical benzils by sodium dithionite (sodium hydrosulfite) in general yields a mixture of isomeric benzoins.Whereas the reduction of aldehydes and ketones by dithionite apparently takes place by a nucleophilic addition mechanism, the reduction of benzils proceeds by an electron-transfer mechanism.The initial product of the reduction is the (Z)-α,α'-stilbenediol which is produced stereospecifically.The ultimate benzoin products, then, result from the two different modes of ketolization of the stilbenediol intermediate.