74684-95-0

Upstream product

• 7525-23-7 4,4'-dimethoxydiphenylmethyl chloride 
• 64-17-5 ethanol 
• 958-80-5 bis(4-methoxyphenyl)thione 
• 728-87-0 4,4'-Dimethoxybenzhydrol 
• 940934-42-9 bis(4-methoxyphenyl)methyl methyl carbonate 
• 1221-72-3 Bis(p-methoxyphenyl)diazomethan 
• 20114-55-0 4,4'-dimethoxybenzophenone hydrazone 
• 714223-45-7 4,4'-dimethoxybenzhydryl 3,5-dinitrobenzoate 
• 116664-86-9 bis(4-methoxyphenyl)methyl 4-cyanophenyl ether 
• 856192-11-5 bis-(4-methoxy-phenyl)-(toluene-4-sulfonyl)-methane 

Relevant academic research and scientific papers

Solvolytic reactivity of pyridinium ions

The leaving group abilities of pyridine, 4-methylpyridine, and 4-chloropyridine in SN1 solvolytic reactions have been determined by analyzing the rate constants of X,Y-substituted benzhydrylpyridinium salts obtained in various solvents. By applying the linear free energy relationship equation, log k = sf (Ef + Nf), the nucleofuge specific parameters of 4-substituted pyridine have been extracted. Because of solvation in the reactant ground state, the reactivity (nucleofugality, Nf) of a given pyridine decreases as the polarity of the solvent increases. High slope parameters (sf > 1) may be due to the spread of the energy levels of the benzhydrylium ion/pyridine pair intermediates in comparison to benzhydrylium ion/chloride pairs (sf ≈ 1). Because of slow heterolysis step of pyridinium salts in various solvents, some are stable under normal conditions.

Substituted diaryldiazomethanes and diazofluorenes: Structure, reactivity and stability

The synthesis of several substituted diaryldiazomethanes and diazofluorenes, and an assessment of their structure, reactivity and stability, is reported.

Selectivity of stabilized benzhydrylium ions

Methyl carbonates (1-4-OCO2Me) and phenyl carbonates (2-4-OCO2Ph) were subjected to solvolysis in the series of aqueous ethanol, the product ratios were determined and the selectivities (k E/kw) of the correspon

Copper(II) bromide as an efficient catalyst for the selective protection and deprotection of alcohols as bis(4-methoxyphenyl)methyl ethers

In a cheap and eco-friendly process, primary and secondary alcohols were easily protected as bis(methoxyphenyl)methyl (BMPM) ethers in good yields using CuBr2 as a catalyst in acetonitrile at room temperature. Deprotection could easily be achie

SN1 reactions with inverse rate profiles

Carbocations may accumulate during solvolysis reactions! The fact that fast ionization followed by slow trapping of the carbocation R+ is a characteristic pattern of many solvolysis reactions requires that the generally accepted energy profiles of these reactions be revised.

Solvent Nucleophilicity

The rates of the reactions of benzhydrylium ions (diarylcarbenium ions) with solvent mixtures of variable composition (water/acetonitrile, methanol/acetonitrile, ethanol/acetonitrile, ethanol/water, and trifluoroethanol/water) have been determined photometrically by conventional UV-vis spectroscopy, stopped-flow methods, and laser flash techniques. It has been shown that the first-order rate constants follow the previously published relationship log k(20°C) = s(N+E), where E is an empirical electrophilicity parameter, N is an empirical nucleophilicity parameter, and s is a nucleophile-specific slope parameter. From plots of log k versus E of the benzhydrylium ions are derived the solvent nucleophilicity parameters s and N, the latter of which are designated as N1 to emphasize that their use in the quoted correlation equation gives rise to first-order rate constants. A linear correlation between N1 and Kevill's solvent nucleophilicity NT based on S-methyldibenzothiophenium ions is reported, which allows one to interconvert the two sets of data. Because the N1 values are directly comparable to the previously reported nucleophilicity parameters N for π-systems (www.cup.uni-muenchen.de/oc/mayr/), the systematic design of Friedel-Crafts reactions with solvolytically generated carbocations becomes possible.

Hydrozirconation of Thioketones. A Simple, Convenient Entry into a Variety of Organosulfur Compounds. An Intersting Ether Synthesis

Aromatic and aliphatic thioketones undergo hydrozirconation at room temperature with (C5H5)2Zr(H)Cl to give sulfur-zirconium compounds, R2CHSZr(Cl)(C5H5)2.Cleavage of the latter by bromine or N-bromosuccinimide affords sulfenyl bromides, acid chlorides give thioesters, methyloxalyl chloride gives a thiooxalate, methyl vinyl ketone results in the formation of the β-keto sulfide, and carbonylation followed by bromination in alcohol affords the ether.Yery mild conditions are utilized for all of these reactions.Mechanisms are proposed for the interesting ether synthesis.