106754-33-0Relevant academic research and scientific papers
Comments on An Article by Francesco Minisci and Francesca Fontana.
Barton, Derek H. R.,Hill, David R.
, p. 1431 - 1434 (1994)
Evidence is summarized to show that the least aspects of Gif chemistry do not involve Fenton-type radical chemistry.
The Fe(III)-Catalyzed Functionalization of Saturated Hydrocarbons by tert-Butyl Hydroperoxide: Mechanistic Studies on the Role of Dioxygen
Barton, Derek H. R.,Beviere, Stephane D.,Chavasiri, Warinthorn,Doller, Dario,Hu, Bin
, p. 5473 - 5476 (1992)
The Fe(III)-catalyzed ketonization of saturated hydrocarbons by tert-butyl hydroperoxide (TBHP) in pyridine-acetic acid or acetonitrile solution follows the reaction pathway alkane -> alkyl hydroperoxide -> ketone or alcohol.Dioxygen (O2) is the precursor of the oxygen atoms in the alkyl hydroperoxide, the alcohol, and the ketone.
Photoinduced direct 4-pyridination of C(sp3)-H Bonds
Hoshikawa, Tamaki,Inoue, Masayuki
, p. 3118 - 3123 (2013/07/26)
Direct substitution of hydrogen in C(sp3)-H bonds by 4-pyridine was achieved by employing benzophenone and 4-cyanopyridine in aqueous acetonitrile under photo-irradiating conditions. This simple and mild 4-pyridination proceeds in a highly chemoselective manner especially at benzylic C(sp3)-H bonds without affecting polar functional groups, and enables intermolecular formation of sterically hindered bonds between alkylaromatics and 4-pyridine. The present methodology thus serves as a powerful tool for construction of biologically active and functional molecules with 4-pyridine substructures.
The functionalization of saturated hydrocarbons. Part 24. The use of tert-butyl hydroperoxide: GoAggIV and GoAggV
Barton, Derek H. R.,Chavasiri, Warinthorn
, p. 19 - 30 (2007/10/02)
The use of tert-butyl hydroperoxide as an oxidant in Gif-type systems (GoAggIV and GoAgfV) catalyzed by various Fe(III) species is examined. Regioselectivity studids of these systems have revealed several characteristics similar to those observed for other prdviously reported Gif-type reactions. A common rdaction pathway for the GoAggIV and GoAggV oxidation systems and other Gif-type reactions (from alkane via alkyl hydroperoxide to ketone or alcohol) is seen.
The functionalization of saturated hydrocarbons. Part 25. Ionic substitution reactions in GoAggIV chemistry: The formation of carbon-halogen bonds
Barton, Derek H. R.,Beviere, Stephane D.,Chavasiri, Warinthorn
, p. 31 - 46 (2007/10/02)
GoAggIV chemistry (Fe (III) species, tert-butyl hydroperoxide in a mixture of pyridine and acetic acid) in the presence of LiCl can transform saturated hydrocarbons efficiently into the corresponding alkyl chlorides. The transformation into monosubstituted alkyl derivatives by "ionic trapping" reagents arising from the interception of the first intermediate of the system supports the presence of a high valent VFe-C species. Mechanistic studies suggest a possible pathway operating via an Fe-centered ligand coupling. In addition, the production of alkyl chlorides and alkyl bromides could also be achieved employing this system in the presence of halogenating reagents such as CCl4 and BrCCl3.
