102-20-5Relevant articles and documents
Oxidation of Alcohols with Peracetic Acid in Ethyl Acetate in the Presence of Sodium Bromide
Morimoto, Takashi,Hirano, Masao,Hamaguchi, Takayoshi,Shimoyama, Masahide,Zhuang, Xiumin
, p. 703 - 706 (1992)
Aliphatic primary alcohols and 1,ω-diols were oxidized to the dimeric esters and lactones, respectively, by peracetic acid in ethyl acetate in the presence of sodium bromide under mild conditions.Aliphatic secondary and benzylic alcohols were converted smoothly to the corresponding carbonyl compounds by the same system.
Synthesis of Unsymmetrical N-Heterocyclic Carbene-Nitrogen-Phosphine Chelated Ruthenium(II) Complexes and Their Reactivity in Acceptorless Dehydrogenative Coupling of Alcohols to Esters
He, Xiaochun,Li, Yaqiu,Fu, Haiyan,Zheng, Xueli,Chen, Hua,Li, Ruixiang,Yu, Xiaojun
, p. 1750 - 1760 (2019)
Two novel ruthenium complexes RuH(CO)Cl(PPh3)(κ2-CP) (1) and [fac-RuH(CO)(PPh3)(κ3-CNP)]Cl (2) bearing unsymmetrical N-heterocyclic carbene-nitrogen-phosphine (CNP) were synthesized and characterized with 1H NMR, 31P NMR, and HRMS. The structure of complex 2 was further confirmed by single-crystal X-ray diffraction. An anion exchange experiment proved that complex 2 could transform into complex 1 in solution. The two complexes exhibited a highly catalytic performance in acceptorless dehydrogenative coupling of alcohols to esters, and the excellent isolated yields of esters were given in a catalyst loading of 1% for para- and meta-substituted benzyl alcohols and long-chain primary alcohols. Although some ortho-substituted benzyl alcohols displayed a relatively low reactivity due to the steric hindrance and the coordination of electron donor with the ruthenium center, the good product yields were still obtained by prolonging the reaction time. Especially, this system successfully realized the dehydrogenative cross-coupling to esters between two different primary alcohols.
RUTHENIUM CATALYZED TRANSFORMATION OF ALCOHOLS TO ESTERS AND LACTONES
Murahashi, Shun-Ichi,Ito, Kei-ichiro,Naota, Takeshi,Maeda, Yoshihiro
, p. 5327 - 5330 (1981)
Homogeneous catalytic oxidative condensation of alcohols and diols to their corresponding esters and lactones has been accomplished using RuH2(PPh3)4.
Spin glass behavior and oxidative catalytic property of Zn2MnO4 from a metathesis driven metastable precursor
Kushwaha, Shreya,Nagarajan, Rajamani
, (2021)
The reaction of chloride salts of zinc and manganese with NaOH yielded a cubic spinel structured metastable precursor at room temperature, driven mainly by the salt elimination process's energetics. While classical drying processes failed to produce the monophasic oxide, recrystallization under the hydrothermal conditions yielded Zn2MnO4 in nano dimensions. The sample consisted of crystallites with an average 6 nm size and had a lattice dimension of 8.396 (13) ?. The selected area electron diffraction pattern reiterated the occurrence of cubic inverse spinel. The presence of fingerprint (A1g and F2g) modes of an inverse spinel at 663 and 561 cm?1 in the Raman spectrum further supported our finding. The TEM-EDS analysis confirmed the ratio of Zn: Mn as 1.95:1. The sample showed an optical bandgap of 2.54 eV. X-ray photoelectron spectral analysis established the existence of manganese in the IV oxidation state. The presence of Mn (IV) with small amounts of Mn (III) (up to 20%) was confirmed from the electron paramagnetic spectra recorded at room temperature and 77 K. An average oxidation state of 3.85 was deduced from the chemical redox titration experiments. The pseudocapacitive behavior of the sample was evident in cyclic voltammetric experiments. The sample exhibited paramagnetic behavior at 298 K within the applied magnetic field of ±50 kOe. In the temperature-dependent measurements, the zero-field and field cooled data points of Zn2MnO4 diverged at 13 K, suggesting a spin-glass behavior. An effective magnetic moment of 4.31 BM was deduced for the sample. The inverse spinel effectively catalyzed the oxidation of phenol. It facilitated nearly 100% degradation of bisphenol-A to salicylaldehyde and phenylethyl alcohol (as major products) in the presence of H2O2 and at a pH of 9.
A TEMPO-like nitroxide combined with an alkyl-substituted pyridine: An efficient catalytic system for the selective oxidation of alcohols with iodine
Kashparova, Vera P.,Klushin, Victor A.,Zhukova, Irina Yu.,Kashparov, Igor S.,Chernysheva, Daria V.,Il'chibaeva, Irina B.,Smirnova, Nina V.,Kagan, Efim Sh.,Chernyshev, Victor M.
, p. 3517 - 3521 (2017)
An efficient method for the oxidation of alcohols to aldehydes or ketones in a two-phase CH2Cl2/NaHCO3 (aq.) system, using iodine and catalytic amounts of 4-acetylamino-2,2,6,6-tetramethylpiperidine-1-oxyl and 2,4,6-trimethylpyridine, was developed. The performance of the method was demonstrated by the selective oxidation of 37 variously substituted alcohols in ≥90% yield, including the gram-scale synthesis of the important chemical 2,5-diformylfuran from biomass-derived 5-hydroxylmethylfurfural.
One-pot electrochemical synthesis of acid anhydrides from alcohols
Kashparova,Papina,Kashparov,Zhukova, I. Yu.,Ilchibaeva,Kagan, E. Sh.
, (2017)
One-pot indirect electrochemical oxidation of alcohols in the methylene chloride–aqueous solution of sodium hydrocarbonate two-phase system in the presence of potassium iodide, 4-acetylamino-2,2,6,6-tetramethylpiperidin-1-oxyl, and 2,6-lutidine results in
Pyridinium chlorochromate catalyzed oxidation of alcohols to aldehydes and ketones with periodic acid
Hunsen, Mo
, p. 1651 - 1653 (2005)
A facile pyridinium chlorochromate (PCC) catalyzed (2 mol %) oxidation of alcohols to ketones and aldehydes using 1.05 equiv of H5IO 6 in acetonitrile is described here.
Oxidative dimerization of primary alcohols to esters catalyzed by iridium complexes
Izumi, Aki,Obora, Yasushi,Sakaguchi, Satoshi,Ishii, Yasutaka
, p. 9199 - 9201 (2006)
Primary alcohols undergo efficiently oxidative dimerization by iridium complexes under air without any solvent to form esters in fair to good yields. For instance, the reaction of 1-dodecanol in the presence of [IrCl(coe)2]2 (3 mol %) at 95 °C for 15 h produced dodecyl dodecanoate in 91% isolated yield. This is the first successful Ir-catalyzed oxidative dimerization of primary alcohols to esters using air as an oxidant. Various primary alcohols are converted to the corresponding esters in fair to good yields.
Oxidative esterification of primary alcohols with TEMPO/CaCl2/Oxone under hydrous conditions
Hackbusch, Sven,Franz, Andreas H.
, p. 2873 - 2876 (2016)
Symmetric esters are important compounds in the chemical industry, which creates demand for simple and efficient synthetic routes. Oxidative esterification is a promising method to achieve these aims. Here, we show that TEMPO/CaCl2/Oxone forms a convenient catalytic system for the synthesis of the aforementioned symmetric esters from primary alcohols in a biphasic dichloromethane-water solvent mixture. The substrate scope of the reaction method is complementary to those previously published and the terminal oxidant appears to play an important role. In addition, the method is shown to oxidize thiols preferentially over alcohol functional groups to give disulfide-bridged compounds.
Staudinger’s phosphazene as an efficient esterifying reagent
Dinesh, Murugan,Ranganathan, Raja,Archana, Sivasubramaniyan,Sathishkumar, Murugan,Roshan Banu, Mohamed Sulthan,Ponnuswamy, Alagusundaram
, p. 1454 - 1460 (2016)
A new application of Staudinger’s phosphazene as an efficient esterifying reagent is reported. Staudinger’s phosphazene formed in situ by the reaction of organic mono-azide with triphenylphosphine, which is trapped by carboxylic acid, to afford amide exclusively. In contrast, interestingly the same phosphazene behaves in a different way as an efficient esterifying reagent, affording ester under a solvent-free microwave-assisted protocol wherein alcohol is added as the another component in addition to the other reactants. This discovery adds yet another new application of Staudinger’s phosphazene to synthetic chemistry.
