81631-43-8Relevant articles and documents
Direct C-H bond activation of ethers and successive C-C bond formation with benzene by a bifunctional palladium-titania photocatalyst
Tyagi, Akanksha,Matsumoto, Tomoya,Kato, Tatsuhisa,Yoshida, Hisao
, p. 4577 - 4583 (2016/07/06)
Palladium-loaded titanium oxide was found to work as a bifunctional photocatalyst for functionalization of benzene with ether upon photoirradiation, without using any special reagents. The metal-loaded TiO2 photocatalyst activated a C-H bond of ethers and the heterogeneous Pd metal nanoparticle catalyst promoted the successive C-C bond formation between benzene and the radical species. In this reaction, benzene reacted very selectively with the α-carbon of various ethers at least in the initial stage of the reaction. Kinetic and ESR studies revealed a detailed mechanism for the reaction.
A Novel Method for the Preparation of Ethers from Carbonyl Compounds with Benzenetellurol Catalyzed by ZnI2
Nagakawa, Keiichi,Osuka, Masahiro,Sasaki, Kazuaki,Aso, Yoshio,Otsubo, Tetsuo,Ogura, Fumio
, p. 1331 - 1334 (2007/10/02)
Benzenetellurol is shown to behave as an effective reagent for the reductive conversion of carbonyl compounds into unsymmetrical ethers under the catalytic influence of ZnI2.
Carbanion Rearrangements by Intramolecular 1,ω Proton Shifts, III. The Reaction of 2-, 3-, 4-, and 5-Phenylalkyllithium Compounds
Maercker, Adalbert,Passlack, Michael
, p. 540 - 577 (2007/10/02)
Upon addition of THF to a solution of 4-phenylbutyllithium (2) in diethyl ether a rapid intramolecular 1,4 proton shift takes place with the formation of 1-phenylbutyllithium (5).Similarly, although somewhat more slowly, 5-phenylpentyllithium (82) rearranges to 1-phenylpentyllithium (83) via 1,5 proton transfer.The corresponding rearrangements by 1,2 or 1,3 hydrogen shifts, however, starting with 2-phenylethyllithium (1) and 3-phenylpropyllithium (54), respectively, were not detected.With 3-phenylpropyllithium (54) a slow intramolecular 1,5 transfer an ortho proton is observed instead, yielding o-propylphenyllithium (100).The corresponding 1,6 shift with 4-phenylbutyllithium (2) was also detected in a minor amount in addition to the 1,4 proton shift already mentioned.There is no indication, however, for a 1,4 transfer of an ortho proton in 2-phenylethyllithium (1).The reaction products in this case can be exclusively explained by intermolecular transmetallation reactions.All ω-phenylalkyllithium compounds under investigation show interesting side and secondary reactions being rather different in deuterated solvents and in deuteriumfree solvents, respectively, due to the isotope effects.The analysis of the products is accomplished by 1H-NMR spectroscopy and, after derivatization, with the help of a GC-MS-combination.Stereoelectronic reasons are made responsible for the failure of the intramolecular 1,2 and 1,3 proton shift in these systems.