63018-83-7Relevant academic research and scientific papers
Structural Dependence in a One-electron Transfer Process: Naphthalene peri Ketones
Sato, Takeo,Kubo, Masao,Nishigaki, Kenji
, p. 815 - 816 (1980)
The cyclic voltammetry of several naphthalene peri ketones was carried out in anhydrous DMF containing TBAP.The cathodic peak potential for carbonyl reduction was found to be shifted toward a more anodic potential when carbonyl, oxygen, and sulfur groups
C-C Bond Cleavage in O-Centered Mono- and Dianions Derived from α-Dicarbonyl Compounds
Varea, Teresa,Medio, Mercedes,Ballesteros, Rafael,Oniga, Ovidiu,Asensio, Gregorio
, p. 10093 - 10100 (2007/10/02)
The reaction of organolithium compounds with oxalyl derivatives and cyclic 1,2-dicarbonyl compounds leads to pinacols or ketones derived from homolytic C-C bond cleavage of the intermediate O,O-centered pinacol dianions depending on the ability of the substituents for the stabilisation of the resulting radical anion.The homolysis is induced by electrostatic repulsion of the negatively charged oxygen atoms.
Magnesium- and Titanium-induced Reductive Coupling of Carbonyl Compounds: Efficient Syntheses of Pinacols and Alkenes
Fuerstner, Alois,Csuk, Rene,Rohrer, Christian,Weidmann, Hans
, p. 1729 - 1734 (2007/10/02)
Finely dispersed magnesium on graphite was found to be a totally selective single-electron transfer reagent of general utility for the reduction of various kinds of carbonyl and dicarbonyl compounds to pinacols, a reaction quite compatible with a number of functional groups.Similarly, titanium on graphite proved to be a universally applicable reducing agent for the efficient conversion of pinacols, carbonyl and dicarbonyl compounds into alkenes and cycloalkenes respectively and for the cyclization of oxo alkanoates to enol ethers, facilitating and unifying the highly useful McMurry reaction.The practicability of the presently known carbonyl coupling methods is discussed in the light of these results.
