16765-45-0

Upstream product

• 7681-84-7 tetrahydrofuran-2-carbaldehyde 
• 5331-61-3 gem-diacetate de tetrahydrofurfural 
• 109-99-9 tetrahydrofuran 
• 100-52-7 benzaldehyde 
• 141957-79-1 phenyl(tetrahydrofuran-2-yl)methanone 
• 4203-44-5 2-phenyltetrahydropyran 
• 13544-26-8 6-phenyl-3,4-dihydro-2H-pyran 
• 93903-57-2 (E)-5-phenylpent-4-en-1-yl 4-methylbenzenesulfonate 

Relevant academic research and scientific papers

Ring-Contraction Reaction of Substituted Tetrahydropyrans via Dehydrogenative Dual Functionalization by Nitrite-Catalyzed Double Activation of Bromine

A nitrite-catalyzed ring contraction reaction of substituted tetrahydrofurans by oxidation of bromide under aerobic conditions as a dehydrogenative dual functionalization was developed to provide 2-acyltetrahydrofurans in good yields. On the other hand, the oxidation reaction of 1-substituted isochromans occurred via the bromohydroxylation to give 1-(dibromoalkyl)-1-hydroxyisochromans in high yields.

Combined Photoredox and Lewis Acid Catalyzed α-Hydroxyalkylation of Cyclic Ethers with Aromatic Ketones

The photochemically induced coupling of aromatic ketones with cyclic ethers such as tetrahydrofuran, tetrahydropyran, and 1,4-dioxane was studied. Direct photolysis of the substrates with UV-A light centered at 350 nm does not lead to photoinduced hydrogen transfer whereas the addition of a mixture of the Lewis acid catalysts Ti(OiPr)4 and BF3 enables the formation of the hydroxyalkylation products.

Chemoselective oxygen-centered radical cyclizations onto silyl enol ethers

(Chemical Equation Presented) A new oxygen-centered radical cyclization onto silyl enol ethers has been developed and utilized for the synthesis of versatile siloxy-substituted tetrahydrofurans. The reactions display excellent chemoselectivity for cyclization onto the electron-rich silyl enol ether when competing terminal alkene cyclization, 1,5-hydrogen abstraction, and β-fragmentation pathways are present. The increased chemoselectivity also allows for the synthesis of tetrahydropyrans, a challenging substrate class to access using oxygen-centered radical alkene cyclizations due to competing 1, 5-hydrogen abstractions.

Hydroxyalkylation of α-C-H bonds of tetrahydrofuran with aldehydes in the presence of triethylborane and tert-butyl hydroperoxide

The α-hydroxyalkylation of tetrahydrofuran with aldehydes via radical C-H abstraction was conducted using triethylborane in the presence of tert-butyl hydroperoxide. This study presents a rare instance of direct intermolecular radical addition of unactivated cyclic ether to aldehydes.

New method for the synthesis of α-substituted tetrahydrofuran -2-methanols through diastereoselective addition of THF to aldehydes mediated by Et3B in the presence of air

The tetrahydrofuranyl radical, generated from THF with Et3B in the presence of air, was found to react with aldehydes threo-selectively to afford α-substituted tetrahydrofuran-2-methanols, the common structural motifs of biologically active ace

DIASTEREOSELECTIVITE DANS LA REACTION DES ORGANOMAGNESIENS SUR LE TETRAHYDROFURFURAL ET SON GEM-DIACETATE EN PRESENCE DE HMPT. ACCES AUX DIOLS-1,2 ERYTHRO.

Grignard Reagents - HMPT complexes have been found to be highly stereoselective reagents for the addition to tetrahydrofurfural and for the substitution of an acetoxy group in tetrahydrofurfural gem-diacetate.In both cases, a high erythro/threo ratio was obtained.