112-12-9Relevant articles and documents
Selective oxidation of alcohols to carbonyl compounds mediated by fluorous-tagged TEMPO radicals
Holczknecht, Orsolya,Cavazzini, Marco,Quici, Silvio,Shepperson, Ian,Pozzi, Gianluca
, p. 677 - 688 (2005)
Oxidation of primary, benzylic and secondary alcohols into their corresponding aldehydes and ketones with safe, inexpensive oxidants was achieved in good yields under mild conditions in the presence of catalytic amounts of 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO) radicals bearing perfluoroalkyl substituents. These "fluorous-tagged" TEMPOs were readily isolated from the reaction products by liquid-liquid or solid-phase extraction, considerably simplifying the purification step. Their recyclability was strongly influenced by the nature of the oxidizing system. The best results were obtained using either [bis(acetoxy)iodo]benzene (BAIB) or aqueous NaOCl as the primary oxidants. Fluorous TEMPO 10 could be reused up to six times in the BAIB oxidation of 1-octanol with only minor loss of catalytic activity.
Experimental and computational study of a direct O2-coupled wacker oxidation: Water dependence in the absence of Cu salts
Anderson, Brian J.,Keith, John A.,Sigman, Matthew S.
, p. 11872 - 11874 (2010)
The kinetics of the Pd[(-)-sparteine]Cl2 catalyzed oxidation of decene using oxygen as the sole oxidant have been studied in the absence of copper salts and high [Cl-]. Saturation kinetics are observed for [decene] as well as a third order dependence on [water]. A mechanism is proposed involving the dissociation of two chlorides and rate-limiting formation of a three-water hydrogen bridged network and subsequent oxypalladation as supported by computational studies.
Imidazolium Dichromate. A New Reagent for the Oxidation of Alcohols to Carbonyl Compounds
Kim, Sunggak,Lhim, Dong Chul
, p. 3297 - 3298 (1986)
Imidazolium dichromate, a stable yellow crystalline compound, is found to bee a mild selective reagent for the oxidation of allylic and benzylic alcohols to the corresponding carbonyl compounds.
Triethylammonium fluorochromate - A new, mild, stable, and inexpensive chromium(VI) oxidant
Ghammamy,Hashemzadeh,Mazareey
, p. 1752 - 1754 (2005)
Triethylammonium fluorochromate was prepared and was used to quantitatively oxidize a number of organic substrates. Triethylammonium fluorochromate is a versatile reagent ensuring effective and selective oxidation of organic compounds, in particular of alcohols, under mild conditions.
Nitrous oxide oxidation of secondary and benzylic alcohols using ruthenium complex catalyst
Hashimoto, Kentaro,Kitaichi, Yasunori,Tanaka, Hirotaka,Ikeno, Taketo,Yamada, Tohru
, p. 922 - 923 (2001)
Catalytic N2O oxidation of various secondary and benzylic alcohols using a ruthenium porphyrin complex is presented. Both secondary and benzylic alcohols were smoothly consumed to give the corresponding ketones and aldehydes in high yields. Nitrous oxide (N2O) is expected to be a new terminal oxidant producing only dinitrogen gas as the only by-product to provide a less wasteful process.
Thiol-functionalized fructose-derived nanoporous carbon as a support for gold nanoparticles and its application for aerobic oxidation of alcohols in water
Mahyari, Mojtaba,Shaabani, Ahmad,Behbahani, Mohammad,Bagheri, Akbar
, p. 576 - 583 (2014)
Gold nanoparticles supported on thiol-functionalized fructose-derived nanoporous carbon (AuNPs@thiol-Fru-d-NPS) were found to be a simple bench-top, biocompatible, recyclable and selective catalytic system for the aerobic oxidation of various types of alcohols into their corresponding aldehydes and ketones at room temperature under the environmentally friendly conditions with excellent yields. Copyright
Aerobic deprotection of monothioacetals catalyzed by trichlorooxyvanadium
Kirihara, Masayuki,Ochiai, Yuta,Arai, Nobuka,Takizawa, Shinobu,Momose, Takefumi,Nemoto, Hideo
, p. 9055 - 9057 (1999)
Monothioacetals are easily deprotected into carbonyls using a catalytic amount of trichlorooxyvanadium under an oxygen atmosphere.
Deprotection of dithioacetals using the tantalum(V) chloride catalyzed oxidation of iodide ion by hydrogen peroxide
Kirihara, Masayuki,Harano, Aiko,Tsukiji, Hiroyuki,Takizawa, Ryu,Uchiyama, Tomoyuki,Hatano, Akihiko
, p. 6377 - 6380 (2005)
Dithioacetals can be deprotected to afford carbonyl groups using the tantalum(V) chloride catalyzed oxidation of iodide ion by hydrogen peroxide under mild conditions.
Synthesis and catalytic activity of a fluorous-tagged TEMPO radical
Pozzi, Gianluca,Cavazzini, Marco,Holczknecht, Orsolya,Quici, Silvio,Shepperson, Ian
, p. 4249 - 4251 (2004)
A fluorous-tagged TEMPO radical has been prepared and its catalytic activity in the chemoselective oxidation of alcohols to carbonyl compounds has been investigated. The new fluorous radical proved to be an efficient, selective and easily recoverable catalyst, which can be conveniently used in standard organic solvents and then isolated and recycled by fluorous liquid-liquid extraction.
A NEW PROCEDURE FOR DETHIOACETALIZATION
Liu, Hsing-Jang,Wiszniewski, Virginia
, p. 5471 - 5474 (1988)
A simple procedure has been developed for the conversion of thioacetals to the corresponding carbonyl compounds using the combination of phenyl dichlorophosphate, dimethylformamide and sodium iodide.
