155200-44-5Relevant articles and documents
Reaction of enol ethers with lead tetraacetate : An improved method for the synthesis of α- methoxy ketones
Singh,Singh,Dikshit
, p. 45 - 49 (1998)
The reaction of cyclic enol ethers with lead tetraacetate in methanol in the presence of BF3.Et2O at 0°C gives α- methoxy cyclic ketones.
New methylene homologation method for cyclic ketones
Liu, Huaqing,Sun, Chunrui,Lee, Nam-Kyu,Henry, Roger F.,Lee, Daesung
supporting information, p. 11889 - 11893 (2012/10/29)
Teaching new tricks to an old dog: By intercepting adducts between ketones and lithium trimethylsilyldiazomethane, a new Tiffeneau-Demjanov type methylene homologation could be realized in a single-step operation. Among proton sources and Lewis acids, silica gel was found to be the most effective reagent for the protonation of intermediates and their subsequent ring expansion (see scheme). Copyright
Ketone homologation to produce α-methoxyketones: Application to conduritol synthesis
Phillipson, Neil,Anson, Michael S.,Montana, John G.,Taylor, Richard J. K.
, p. 2821 - 2829 (2007/10/03)
The scope of Trost's sulfone homologation procedure for the conversion of ketones into their α-methoxylated higher homologues has been dramatically expanded. The use of zirconium (or hafnium) tetrachloride in the hydroxy sulfone rearrangement step gives g
α-Methoxyketone Synthesis via Ketone Homologation: ZrCl4-Mediated Hydroxy Sulfone Rearrangements
Montana, John G.,Phillipson, Neil,Taylor, Richard J. K.
, p. 2289 - 2290 (2007/10/02)
The adducts between ketones and the anion derived from benzene undergo efficient, regioselective rearrangement to give α-methoxyketones when treated with ZrCl4 and HfCl4; this new procedure allows the sulfone-mediated homologation
ERZEUGUNG UND CYCLOADDITION VON ALLYLIUMIONEN AUS α-HALOGENKETONEN UNTER SOLVOLYSE-BEDINGUNGEN
Foehlisch, Baldur,Gottstein, Wolfgang,Kaiser, Roland,Wanner, Iris
, p. 3005 - 3009 (2007/10/02)
Some α-haloketones react with furan in methanolic solution in the presence of base to form the 3-oxo-8-oxabicyclooct-6-enes (11), the products derived from a cycloaddition of an allylium intermediate (5 or 6).
Mechanism of the Photochemical Wolff Rearrangement. The Role of Conformation in the Photolysis of α-Diazo Carbonyl Compounds.
Tomioka, Hideo,Okuno, Hiroshi,Izawa, Yasuji
, p. 5278 - 5283 (2007/10/02)
Investigation of photochemical processes of several α-diazo carbonyl compounds reveals that the Wolff rearrangement to form ketene takes place directly from the singlet excited state of the s-Z conformer whereas the excited state of the s-E conformer dissociates nitrogen to generate singlet carbonyl carbene, which either undergoes characteristic carbenic reactions, e.g., insertion and 1,2-hydrogen shift, or gives rise to ketene.The migratory aptitude as well as the relative efficiency of other competing reactions from singlet carbene is shown to be an important factor in dete rmining which reaction pathway is favored.Substantial amounts of singlet carbene can be formed even under sensitized conditions, presumably via intersystem crossing from initially formed triplet carbene.