25330-02-3Relevant academic research and scientific papers
Combined Photoredox and Lewis Acid Catalyzed α-Hydroxyalkylation of Cyclic Ethers with Aromatic Ketones
Reckenth?ler, Melissa,Neud?rfl, J?rg-M.,Zorlu, Elif,Griesbeck, Axel G.
, p. 7211 - 7216 (2016/09/04)
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.
A photochemical entry to depsides: Synthesis of gustastatin
Garcia-Fortanet, Jorge,Debergh, John R.,De Brabander, Jef K.
, p. 685 - 688 (2007/10/03)
(Chemical Equation Presented) Herein, we propose a modular and general strategy to construct orcinol-type depsides based on the photolysis of functionalized benzodioxinones (I). Notably, resorcinylic esters are obtained without competing isocoumarin (II) formation, exemplified by the first total synthesis of gustastatin in 10 steps from commercially available trihydroxybenzoic acid.
AN EFFICIENT ACCEPTOR OF 1-HYDROXY(OR ALKOXY)ALKYL RADICALS -- KETENE DITHIOACETAL S,S-DIOXIDE --
Ogura, Katsuyuki,Yanagisawa, Atsushi,Fujino, Takeo,Takahashi, Kazumasa
, p. 5387 - 5390 (2007/10/02)
Irradiation of a ketene dithioacetal S,S-dioxide (2) in alcohols or ethers containing benzophenone gave an adduct which was formed by addition of 1-hydroxy- or 1-alkoxyalkyl radicals to 2 followed by hydrogen transfer.
RADICAL-ANIONS OF AROMATIC COMPOUNDS. V. EFFECT OF THE STRUCTURE OF THE ELECTROPHILE ON THE RATIO OF THE ELECTRON-DONATING AND NUCLEOPHILIC CHARACTERISTICS OF THE BENZOPHENONE RADICAL-ANION IN REACTIONS WITH N,N,N-TRIMETHYLARYLAMMONIUM PERCHLORATES
Selivanov, B. A.,Bil'kis, I. I.,Varand, V. L.,Shteingarts, V. D.
, p. 865 - 877 (2007/10/02)
In reaction with N,N,N-trimethylammonium perchlorates in THF the potassium salt of the benzophenone radical-anion exhibits dual reactivity, acting both as nucleophile (as SN process) and as a one-electron reducing agent (an ET process).The effect of the structure of the aryl fragment of the ammonium salt on the ratio of the rates WET/WSN is determined by the higher sensitivity of the electron transfer rate to the effect of this factor compared with nucleophilic substitution and varies in the following order: p-Methoxyphenyl p-tolyl m-tolyl phenyl m-methoxyphenyl p-biphenylyl m-chlorophenyl 1-naphthyl.I t was found that the structure of the aryl fragment of the ammonium salt has a significant effect on the regioselectivity of the methylation of the benzophenone radical-anion.
ELECTRON-TRANSFER PHOTOOXYGENATION. 8. TRAPPING OF INTERNAL NUCLEOPHILES
Jiang, Z. Q.,Foote, C. S.
, p. 461 - 464 (2007/10/02)
Irradiation of 5,5-diphenylpent-4-en-1-ol, sensitized by 9,10-dicyanoanthracene under N2, leads to 2-(diphenylmethyl)-tetrahydrofuran (7).Under O2, a related oxidation product, 2-(diphenylhydroxymethyl)-tetrahydrofuran is produced.
