514-15-8Relevant articles and documents
A Highly Selective Na2WO4-Catalyzed Oxidation of Terpenic Alcohols by Hydrogen Peroxide
Viana, Luna Andrade Silva,da Silva, Giovanna Rodrigues Nobile,da Silva, Márcio Jose
, p. 374 - 382 (2017/12/04)
Sodium tungstate was found to be an active and highly selective catalyst to oxidation of various primary or secondary origin renewable alcohols by hydrogen peroxide as green oxidant. Borneol, nerol, geraniol and β-citronellol were efficiently and selectively converted to respective carbonyl derivatives by hydrogen peroxide. ATR/FT-IR measurements confirmed that Na2W(O2)4 was the specie active catalytically. The role of the main reaction variables, including temperature, reactants and catalyst concentration, solvent, and nature of substrate were also assessed. In addition to use a green oxidant, this simple and environmentally friendly catalyst system did not require additive to control pH, molecular sieves or phase transfer catalyst. Graphical Abstract: [Figure not available: see fulltext.].
Chloroform as a hydrogen atom donor in barton reductive decarboxylation reactions
Ho, Junming,Zheng, Jingjing,Meana-Paneda, Ruben,Truhlar, Donald G.,Ko, Eun Jung,Savage, G. Paul,Williams, Craig M.,Coote, Michelle L.,Tsanaktsidis, John
, p. 6677 - 6687 (2013/07/26)
The utility of chloroform as both a solvent and a hydrogen atom donor in Barton reductive decarboxylation of a range of carboxylic acids was recently demonstrated (Ko, E. J. et al. Org. Lett. 2011, 13, 1944). In the present work, a combination of electronic structure calculations, direct dynamics calculations, and experimental studies was carried out to investigate how chloroform acts as a hydrogen atom donor in Barton reductive decarboxylations and to determine the scope of this process. The results from this study show that hydrogen atom transfer from chloroform occurs directly under kinetic control and is aided by a combination of polar effects and quantum mechanical tunneling. Chloroform acts as an effective hydrogen atom donor for primary, secondary, and tertiary alkyl radicals, although significant chlorination was also observed with unstrained tertiary carboxylic acids.
Iodine(V)/ruthenium(III)-cocatalyzed oxidations: A highly efficient tandem catalytic system for the oxidation of alcohols and hydrocarbons with oxone
Yusubov, Mekhman S.,Zagulyaeva, Aleksandra A.,Zhdankin, Viktor V.
supporting information; experimental part, p. 11091 - 11094 (2010/04/28)
An extremely mild and efficient tandem catalytic system for the oxidation of alcohols and hydrocarbons based on Ru(III)-catalyzed reoxidation of ArIO to ArIO2 was reported, by using Oxone as a stoichiometric oxidant. Oxone was added to a mixture of propylbenzene, PhI, and RuCl3 in acetonitrile and water in five portions over 22 h under stirring at room temperature. The reaction mixture was stirred for an additional 4 h and was monitored by TLC by the disappearance of propylbenzene. Then ethyl acetate and water were added and the mixture was stirred for 5 mm. The organic solution was separated and the aqueous phase was extracted with ethyl acetate. The organic phases were combined, washed with NaCl, and dried over Na2SO 4. The oxidation of the other hydrocarbons was performed by using a similar procedure. The use of smaller amounts of Oxone led to incomplete conversion owing to its noticeable decomposition with loss of oxygen gas under reaction conditions.
