15018-12-9Relevant academic research and scientific papers
Reductive etherification of aldehydes photocatalyzed by dicarbonyl pentamethylcyclopentadienyl iron complexes
Argouarch, Gilles,Grelaud, Guillaume,Roisnel, Thierry,Humphrey, Mark G.,Paul, Frédéric
supporting information, p. 5015 - 5018 (2012/11/07)
The reductive etherification of aldehydes can be performed by the reaction with dialkylmethylsilanes in the presence of new iron(II) piano-stool catalysts of general formula Cp*Fe(CO)2Ar (Cp * = η5-C5Me5; Ar = Ph, 4-C6H4OCH3, 4-C6H4CH 3, Fc). This transformation is promoted by UV light and affords a simple route for the preparation of unsymmetrical alkyl ethers.
Intramolecular rearrangements of but-3-enoic esters
Tsaconas, Michael,Prager, Rolf H.,Millan, David S.
, p. 435 - 437 (2007/10/03)
Support for the proposal by Khalafy and Prager1 of a cheletropic rearrangement of a 6-methylidenecyclohexa-2,4-diene-1-carboxylate under flash vacuum pyrolysis (f.v.p.) conditions has been obtained by a study of the f.v.p. products obtained from methyl 1-methyl-6-methylidenecyclohexa-2,4-diene-1-carboxylate and methyl 2,2-dimethylbut-3-enoate. A significant product in each case arises from a reaction involving decarbonylation and transfer of a methoxy group to C4 (but-3-enoate numbering). CSIRO 2000.
A convenient synthesis of methyl- and isopropyl-benzyl ethers using silver(II) oxide as reagent
Ortiz,Walls,Yuste,Barrios,Sanchez-Obregon,Pinelo
, p. 749 - 756 (2007/10/02)
Substituted bromomethyl- and chloromethylbenzenes and bis(bromomethyl) benzenes were directly converted, in high yields, to the corresponding methyl- and isopropyl-benzyl ethers by treatment with silver(II) oxide in methanol or isopropanol.
Intramolecular Generation of Oxonium Ylides from Functionalized Arylcarbenes
Kirmse, Wolfgang,Kund, Klaus
, p. 1465 - 1473 (2007/10/02)
Arylcarbenes carrying alkoxyalkyl groups in the ortho position have been generated by flash pyrolysis and photolysis of appropriate tosylhydrazone sodium salts.In the gas phase and in a aprotic solvents, interaction of the carbenes with the lone electron pairs of oxygen competes efficiently with insertion into C-H bonds.Both five- and six-membered cyclic oxonium ylides have been generated.The ylides 23, 37, 61b, and 74 undergo 1,2 shifts of benzyl groups with ease, even if ring contraction to highly strained benzocyclobutenes is involved (23, 74).The oxonium ylides37 and 61b strongly prefer the nonconcerted Stevens rearrangement to the sigmatropic Sommelet rearrangement, in contrast to analogous ammonium ylides.Alkyl shifts occur to a very minor extent, if at all.Evidence is presented that alcohols intercept both the carbenes and the oxonium ylides.Protonation of the ylides leads to cyclic oxonium ions, which undergo nucleophilic cleavage of the C-O bonds.Acid catalyzed decomposition of the appropriate diazo compounds gives rise to six-membered, but not to five-membered, cyclic oxonium ions, thus confirming the different intramolecular reactivities of arylcarbenes and benzyl cations.The efficiency of carbene interception increases with increasing acidity of the medium, suggesting nucleophilic behavior (protonation) of the arylcarbenes.
A NOVEL METHOXYMETHYLATION OF ARYL BROMIDE BY METHOXYMETHYLTRIBUTYLTIN IN THE PRESENCE OF PALLADIUM COMPLEX
Kosugi, Masanori,Sumiya, Takashi,Ogata, Toshimi,Sano, Hiroshi,Migita, Toshihiko
, p. 1225 - 1226 (2007/10/02)
The reaction of aryl bromides with methoxymethyltributyltin in the presence of a catalytic amount of dichlorobis(triphenylphosphine)palladium was found to give arylmethyl methyl ether.The reaction is a novel aromatic methoxymethylation.
