65662-59-1Relevant articles and documents
A high performance oxidation method for secondary alcohols by inductive activation of TEMPO in combination with pyridine-bromine complexes
Mei, Zhen-Wu,Omote, Takumi,Mansour, Mounir,Kawafuchi, Hiroyuki,Takaguchi, Yutaka,Jutand, Anny,Tsuboi, Sadao,Inokuchi, Tsutomu
experimental part, p. 10761 - 10766 (2009/04/11)
A new TEMPO-mediated catalytic oxidation method in combination with Py·HBr3 (stoichiometric) is developed for oxidation of secondary alcohols to the corresponding ketones. The performance of this oxidizing system is better compared with that of TEMPO method combined with R4NBr3. Poly(4-vinylpyridine)·HBr3 can be used in place of Py·HBr3. The electron-withdrawing substituent at the C-4 position of TEMPO increases the reactivity of TEMPO significantly in the oxidation of electron-deficient alcohols such as polyhaloalkylmethanols. Inductive effect of the substituent of TEMPO is discussed through the characterization of the redox potential of N-O radical by cyclic voltammetry.
1-BENZYL-1,4-DIHYDRONICOTINAMIDE AS A REAGENT FOR REPLACING ALIPHATIC NITRO GROUPS BY HYDROGEN. AN ELECTRON-TRANSFER CHAIN REACTION.
Ono,Tamura,Kaji
, p. 4017 - 4022 (2007/10/02)
The reaction of alpha -nitro nitriles, alpha -nitro esters, and alpha -nitro ketones with 1-benzyl-1,4-dihydronicotinamide (BNAH) can occur with selective replacement of the nitro group by hydrogen without affecting other functional groups. Evidence is presented to support the claim that the reaction proceeds via an electron-transfer chain mechanism in which radical anions and free radicals are intermediates.