84801-15-0Relevant academic research and scientific papers
A survey of sulfide ligands for allylic C-H oxidations of terminal olefins
Le, Chichip Q.,Kunchithapatham, Kamala,Henderson, William H.,Check, Christopher T.,Stambuli, James P.
supporting information, p. 11153 - 11157 (2013/09/02)
Perfect to a THT! Screening a diverse library of thioether ligands led to the discovery of tetrahydrothiophene (THT) as a highly reactive and selective ligand for Pd-catalyzed allylic C-H oxidation reactions (see scheme). This novel ligand system provides some of the highest reported yields for the formation of (E)-linear allylic acetates through allylic C-H activation chemistry (BQ = 1,4-benzoquinone). Copyright
Allylic oxidations of terminal olefins using a palladium thioether catalyst
Henderson, William H.,Check, Christopher T.,Proust, Nicolas,Stambuli, James P.
supporting information; scheme or table, p. 824 - 827 (2010/04/06)
"Chemical equation presented" A palladium catalyst that converts terminal olefins to linear allylic acetates at lower catalyst loadings and faster reaction times than current systems is reported. This reaction can be conducted using benzoquinone as the oxidizing agent or catalytic amounts of copper and hydroquinone under one atmosphere of oxygen. Preliminary reactivity studies of π-allylpalladium complexes under our reaction conditions do not provide results similar to those obtained in the catalytic reaction, which may suggest an alternative reaction pathway. The palladium catalyst is ligated by an aryloxyalkyl aryl sulfide, which is identified as a new ligand for homogeneous catalysis.
Conformational mobility and preferences of Allyl-type organometallic intermediates : Dodec-2-eny lpotassium
Franzini, Livia,Moret, Etienne,Schlosser, Manfred
, p. 83 - 87 (2007/10/03)
Alk-2-enylpotassium compounds having the endo conformation are synthetically very valuable precursors of (Z)-olefinic derivatives substituted at the outward allylic position. They may be generated by "stereoconservative" metalation of the readily available (Z)-alk-2-enes by using the superbasic mixture of butyllithium and potassium terf-butoxide or by metalation under similar conditions of stereorandom mixtures of alk-2-enes or alk-1-enes followed by torsional isomerization of the concomitantly formed exo conformers to the thermodynamically more stable endo species. The principal factors that dictate the rate and the extent of the endo/exo equilibration are the substrate geometry, the solvent, the temperature, the reagent stoichiometry, and catalysis Keywords: Torsional (ZIE) isomerization / Selectivity, regio- and stereo- / Allylsilanes / Allylic oxidation VCH Verlagsgescllschaft mbH.
Regiospecific Preparation of Primary Allyl Acetates (2-Alkenyl Acetates)
Martinez, Antonio Garcia,Villalobos, Angeles Cruces,Ruiz, Manuel Oliver
, p. 58 - 60 (2007/10/02)
The reaction of primary, secondary and tertiary allyl alcohols 1 with anhydrous magnesium iodide in benzene gives regiospecifically the primary allyl iodides 2.The corresponding primary allyl acetates 3 are obtained regiospecifically by reaction of 2 with anhydrous sodium acetate in dimethylformamide.
