57917-94-9

Upstream product

• 67-56-1 methanol 
• 41683-70-9 1,2-diphenyl-1-diazopropane 
• 57917-93-8 erythro-1,2-Diphenyl-1-methoxy-3-(chloromercuri)propane 
• 57917-93-8 threo-1,2-Diphenyl-1-methoxy-3-(chloromercuri)propane 
• 5292-20-6 α-methyl-β,β-diphenylpropionic acid 

Relevant academic research and scientific papers

Electrochemical oxidative decarboxylation and 1,2-aryl migration towards the synthesis of 1,2-diaryl ethers

Carboxylic acid compounds are important chemicals and are widely present in various natural products. They are not only nucleophiles, but also radical precursors. Classic transition-metal-catalyzed and photochemical decarboxylation have shown their excellent site selectivity in radical chemistry. However, electrochemical decarboxylation with a long history hasn't got enough attention in recent years. In this work, the electrochemical oxidative decarboxylation and 1,2-aryl migration of 3,3-diarylpropionic acids have been introduced to construct C-O bonds with alcohols. Remarkably, this transformation can proceed smoothly without metal catalysts and external oxidants.

Excited Precursor Reactivity, Fast 1,2-H Shifts, and Diffusion-Controlled Methanol Insertion in 1,2-Diphenylalkylidenes

The photochemistry of several arylalkyldiazo compounds has been investigated by steady-state direct and triplet sensitized irradiations and by nanosecond laser flash photolysis. Steady-state photolyses in methanol yielded methyl ethers and alkenes as the only significant products. Ethers were formed by denitrogenation of the diazo compound followed by carbene insertion into the MeO-H bond, and alkenes were obtained by 1,2-R (R = H,Ph) migrations both in the free carbene and in the singlet excited state of the diazo precursor. Evidence for the exited-state precursor reaction came from differences in product yields as a function of excitation wavelength and excited-state multiplicity. The yields of methyl ethers increased with increasing excitation wavelengths and were greatest upon triplet-state sensitization but were never the sole products formed despite expected diffusion-controlled insertion rates. Accordingly, the formation of pyridine ylides analyzed by laser flash photolysis in the presence of high concentrations of the base yielded relatively modest transient absorptions. The kinetics of the 1,2-H reaction, analyzed by time-resolved detection of stilbene in the case of 1,2-diphenylethylidenes, displayed fast and slow components. The fast component was attributed to stilbene that formed from the excited-state precursor and from the originally formed singlet carbene within the 20 ns pulse. The long-lived component was attributed to a spin-state equilibrated carbene with a lifetime of 70-80 ns in fluorocarbon solvents. Analysis of the long-lived component by a Stern-Volmer treatment upon addition of MeOH gave a lower limit for the reaction rate constant with a value of k1,2-H > 5 × 109 s-1 in a mixed Freon-methanol solvent. It is concluded that the combined effect of phenyl substituents at the carbon bearing the migrating group and high solvent polarity can lead to intramolecular 1,2-H shifts and 1,2-Ph migrations that are fast enough to compete with diffusion-controlled intermolecular MeO-H insertion in concentrated MeOH solutions.

Oxymetylation. 21. Regioselectivity, Rearrangement, and Direct 1,2-Dioxolane Formation in the Peroxymercuriation of cis- and trans-1,2-Diphenylcyclopropane

The regiochemistry and stereochemistry of the peroxymercuriation of trans- and cis-1,2-diphenylcyclopropane (1a,b) have been determined.The trans isomer reacted exclusively by 1,3-bond scission to give the threo and erythro γ-peroxymercurials (3a,b) along

Stereochemistry of Ring Opening of trans-1,2-Diphenylcyclopropanes by Mercury(II)salts

Reaction of trans-1,2-diphenylcyclopropanes 1 and 2 with mercuric salts yields diastereomeric 1,2-diphenylpropanole derivatives.The ratio of erythro and threo diastereomers depends on the nature of substituents and solvent properties.A mechanism is propos