57646-22-7

Upstream product

• 91-01-0 1,1-Diphenylmethanol 
• 1547-96-2 2,4,6-tris(2,2,2-trifluoroethoxy)-1,3,5-triazine 
• 75-89-8 2,2,2-trifluoroethanol 
• 5350-57-2 benzophenone hydrazone 
• 119-61-9 benzophenone 
• 908093-98-1 diazodiphenylmethane 
• 90-99-3 diphenylchloromethane 
• 64-17-5 ethanol 
• 896-65-1 (1,2-diphenylcyclopropyl)benzene 
• 371-67-5 2,2,2-trifluorodiazoethane 
• 709-82-0 diphenylmethinium 

Relevant academic research and scientific papers

Proton or Carbene Transfer? On the Dark and Light Reaction of Diazoalkanes with Alcohols

The formal alkylation reaction of OH groups with diazoalkanes under catalyst-free reaction conditions finds broad application in organic synthesis. However, even today, this reaction is mainly limited to the use of diazomethane as reaction partner. In thi

Aryl Boronic Acid Catalysed Dehydrative Substitution of Benzylic Alcohols for C?O Bond Formation

A combination of pentafluorophenylboronic acid and oxalic acid catalyses the dehydrative substitution of benzylic alcohols with a second alcohol to form new C?O bonds. This method has been applied to the intermolecular substitution of benzylic alcohols to form symmetrical ethers, intramolecular cyclisations of diols to form aryl-substituted tetrahydrofuran and tetrahydropyran derivatives, and intermolecular crossed-etherification reactions between two different alcohols. Mechanistic control experiments have identified a potential catalytic intermediate formed between the aryl boronic acid and oxalic acid.

Why are vinyl cations sluggish electrophiles?

The kinetics of the reactions of the vinyl cations 2 [Ph2C=C+-(4-MeO-C6H4)] and 3 [Me2C=C+-(4-MeO-C6H4)] (generated by laser flash photolysis) with diverse nucleophile

Boron Trifluoride?Diethyl Ether-Catalyzed Etherification of Alcohols: A Metal-Free Pathway to Diphenylmethyl Ethers

A novel boron trifluoride?diethyl ether (BF3?OEt2)-catalyzed etherification procedure has been developed in which primary and secondary alcohols are easily converted into diphenylmethyl ethers with yields of up to 99%.

Expedient and efficient one pot synthesis of trifluoroethyl ethers from metal free 2,4,6-tris-(2,2,2-trifluoro-ethoxy)-[1,3,5] triazene

An efficient synthesis of fluorinated alkyl and aryl ethers was achieved by the use of s-triazene derived fluorinated reagent 2,4,6-tris-(2,2,2-trifluoro-ethoxy)-[1,3,5] triazene (TriTFET). The procedure offers a very attractive alternative for the synthesis of fluorinated motifs that are found in various bioactive molecules. Moreover, TriTFET is a synthetic non-toxic, non-ozone depleting and stable reagent. All compounds were characterized by 1H, 13C and 19F NMR.

Solvolytic Reactions in Fluorinated Alcohols. Role of Nucleophilic and Other Solvation Effects

Rate constants and products for solvolyses of chlorodiphenylmethane (Ph2CHCl) and p-methoxybenzyl chloride in 2,2,2-trifluoroethanol (TFE)/water and TFE/ethanol are reported, along with additional kinetic data for solvolyses of tert-butyl and other alkyl halides (RX) in 97% w/w TFE/water and in 97% w/w hexafluoropropan-2-ol/water (HFIP). Results are discussed in terms of the solvent ionizing power (Y) and the solvent nucleophilicity (N), and contributions from other solvation effects are considered. Comparisons with other SN1 solvolyses show that solvolyses of Ph2CHCl in TFE mixtures are unexpectedly fast, but product ratios are unexceptional. An additional solvation effect influences solvolyses leading to delocalized cations, and a delocalized cationic transition state for concerted elimination may explain the recent results of Takeuchi et al., (J. Org. Chem. 1997, 62, 4904) without the need to postulate additional specific solvation effects for adamantyl systems, such as Bronsted-base solvation of α- and β-hydrogen atoms; concerted elimination may occur because simple tertiary alkyl cations are too unstable to form in predominantly aqueous media. Iodide/bromide and bromide/chloride rate ratios are very similar for 1-adamantyl halides and corresponding solvolyses of tert-butyl halides; these ratios decrease in the order aq EtOH > TFE > HFIP, as expected for an electrophilic solvation effect (this effect can readily be incorporated into Y values). From kinetic data for a series of tertiary alkyl chlorides in 97% TFE/water, it is shown that the susceptibility of rates of solvolyses of RCl to N decreases with an increase in steric hindrance or with an increase in charge stabilization. Also, the small kinetic solvent isotope effects for typical solvolyses (e.g., methyl tosylate) indicate that nucleophilic attack lags behind heterolysis of the C-X bond.

Effects of Aryl Substituents on Electron-Transfer-Mediated Photochemical Addition of Alcohol to 1,1,2-Triarylcyclopropanes

Direct irradiation of 1,1,2-triarylcyclopropanes in alcohol resulted in the formation of all possible products arising from trimethylene biradicals, while DCB-sensitised irradiation gave a novel "anti-Markownikoff" addition product of alcohol almost exclusively.In order to get insight into the nature and fate of intermediates in the reactions, the effects of nucleophiles and aryl substituents are examined.

Acid-Catalyzed Reaction of 2,2,2-Trifluorodiazoethane for Analysis of Functional Groups by 19F Nuclear Magnetic Resonance Spectrometry

The acid-catalyzed reactions of trifluorodiazoethane with alcohols, phenols, thiols, and carboxylic acids are reported.The yield data for these trifluoroethyl derivatives suggest a simple, and in many cases, quantitative method for introduction of a fluorine tagging group.The 19F chemical shifts indicate that most functional groups (e.g., phenols, alcohols, etc.) have fairly well resolved chemical shifts regions.In addition, paramagnetic shift reagents have been utilized to selectively differentiate carboxylic acids from other active hydrogen functional groups.