10442-33-8

Usage

Uses

Used in Organic Synthesis:
3,4-diphenylhexane-3,4-diol is utilized as a reagent in organic synthesis for its ability to participate in a wide range of chemical reactions, facilitating the creation of diverse organic compounds.
Used as an Intermediate in Chemical Production:
In the chemical industry, 3,4-diphenylhexane-3,4-diol serves as an intermediate, playing a crucial role in the production of other chemicals, highlighting its importance in the synthesis of complex molecules.
Used in Polymer Production:
3,4-diphenylhexane-3,4-diol is employed in the production of polymers, capitalizing on its structural properties to contribute to the formation of polymeric materials with specific characteristics.
Used as a Building Block in Organic Compound Synthesis:
Recognized for its versatile properties, 3,4-diphenylhexane-3,4-diol is used as a building block in the synthesis of various organic compounds, underlining its value in constructing novel molecular structures for different applications across industries.

Upstream product

• 64-17-5 ethanol 
• 93-55-0 1-phenyl-propan-1-one 
• 93-54-9 1-Phenyl-1-propanol 
• 98-86-2 acetophenone 
• 54589-41-2 (4-(benzyloxy)phenyl)(phenyl)methanone 
• 60-29-7 diethyl ether 
• 98-85-1 1-Phenylethanol 
• 1636-34-6 2,3-diphenyl-2,3-butanediol 

Downstream Products

• 93-55-0 1-phenyl-propan-1-one 
• 24815-65-4 (E,E)-3,4-diphenyl-2,4-hexadiene 

Relevant academic research and scientific papers

Highly regioselective and chemoselective titanocene mediated Barbier-type allylation reactions

Titanocene carboxylate 1 is an excellent chemoselective reagent for unprecedented α-regioselective Barbier-type reactions. It constitutes the first titanocene(iii) able to tolerate epoxides and readily reduced carbonyl compounds, such as aromatic and α,β-unsaturated aldehydes. The Royal Society of Chemistry.

Enantioselective cathodic reduction of some prochiral ketones in the presence of (1R,2S)-(-)-N,N-dimethylephedrinium tetrafluoroborate at a mercury pool cathode

The enantioselective cathodic reduction of some prochiral ketones viz. acetophenone (I), propiophenone (II), butyrophenone (III), valerophenone (IV), isobutyrophenone (V), and pivalophenone (VI) has been accomplished at a mercury pool cathode in N,N-dimethylformamide (DMF)-water (90:10) using tetrabutylammonium fluoroborate (TBA·BF4) as a supporting electrolyte in the presence of (1R,2S)-(-)-N,N-dimethylephedrinium tetrafluoroborate (DET). Cyclic voltammetric investigations have been carried out and a probable mechanism of the process has been presented.

Efficient method for pinacol coupling of aromatic and aliphatic ketones by using titanium(II) chloride and zinc in the presence of pivalonitrile

The reductive coupling reaction of aromatic and aliphatic ketones including acyclic aliphatic ketones proceeded smoothly to give the corresponding pinacols in good to high yields below room temperature by the combined use of titanium(II) chloride and zinc in the presence of pivalonitrile. Meso-selective formation of the coupling products was observed in the cases with some acyclic aliphatic ketones.

Preparation of Samarium(II) Triflate and It Mediated Grignard-type Reaction. In Situ Formation and Reaction of New Organosamarium Reagents

Samarium(II) triflate was readily prepared by reaction of samarium(III) triflate with sec-butyllithium at room temperature in THF.Its reducing ability was examined by pinacol coupling of carbonyl compounds.Sm(OTf)2 mediated Grignard-type reaction in THF-HMPA effectively; alkylation and allylation of ketones or aldehydes by simple alkyl, allyl, and benzyl halides proceeded via organosamarium intermediates.

Rate Constants for Degenerate Hydrogen Atom Exchange between α-Hydroxy Radicals and Ketones

When a phenyl ketone is irradiated in the presence of 1-phenylethanol, the photoproducts include acetophenone pinacol, the pinacol from the other phenyl ketone, a mixed pinacol, and acetophenone, which is formed by irreversible hydrogen atom exchange between the hemipinacol radical of acetophenone and the other ketone.Rate constants for this hydrogen atom exchange between the hemipinacol radical of acetophenone and three other ketones were determined by measuring how acetophenone yields depend on the concentration of the other ketone.Comparable measurements were made for p-chloroacetophenone formation by irradiating acetophenone in the presence of 1-(p-chlorophenyl)ethanol.As the starting ketone concentration increases, so does the amount of exchange relative to pinacol, while the pinacol content reflects decreasing amounts of the original alcohol.Exchange is measurable at ketone concentrations below 0.01 M and is complete by 0.1 M.Rate constants kex of 3.7, 6.3, 4.2, and 8.6 * 103 M-1 s-1 were deduced for hydrogen transfer to propiophenone, isobutyrophenone, p-methylacetophenone, and p-chloroacetophenone, respectively, based on a competing rate constant for radical coupling of 2 * 109 M-1 s-1.Equilibrium constants for the hydrogen transfer were determined from the product ratios obtained by irradiating a mixture of two ketones with 2-propanol; from these k-ex values of 11.5, 57, 13, and 1.8 * 103 M-1 s-1, respectively, were deduced for hydrogen transfer to acetophenone from the four other ketone hemipinacol radicals.These exchange rate constants depend more on the structure of the radical than on that of the ketone.Actual quantum yields for pinacol formation do not exceed 50 percent ; this maximum quantum efficiency rises to 71 percent for 1-phenylethanol-O-d.From this inverse isotope effect it is concluded that half the reaction of triplet acetophenone with 1-phenylethanol involves abstraction of an OH hydrogen followed by disproportionation of the initial radical pair back to reactants.

REDUCTIVE COUPLING OF CARBONYL COMPOUNDS TO PINACOLS BY USING LOW-VALENT CERIUM

Aldehydes and ketones, on treatment with a low-valent cerium reagent, undergo reductive dimerization to produce the corresponding pinacols in high yield.