104-88-1Relevant articles and documents
Catalytic oxidation of benzyl alcohols by new Cu(II) complexes of 1,3-oxazolidine based ligand obtained from a solvent free reaction
Bikas, Rahman,Ajormal, Fatemeh,Emami, Marzieh,Noshiranzadeh, Nader,Kozakiewicz, Anna
, p. 77 - 87 (2018)
A new 1,3-oxazolidine based ligand, (2-pyridin-2-yl-1,3-oxazolidine-4,4-diyl)dimethanol (H3L), has been synthesized from the reaction of 2-amino-2-(hydroxymethyl)-1,3-propanediol and 2-pyridinecarboxaldehyde at 110 °C. Two mononuclear Cu(II) complexes, [Cu(H3L)Cl2]·CH3OH (1) and [Cu(H3L)2]·2Cl (2), have been synthesized with a similar procedure by the reaction of H3L and CuCl2·H2O in 1:1 and 2:1 M ratios in methanol. The ligand and complexes have been characterized by elemental analysis and spectroscopic methods. The structure of complexes has been characterized by single-crystal X-ray diffraction analysis which showed the copper ion has a distorted square pyramidal geometry in 1 and distorted octahedral geometry in 2. The 1,3-oxazolidine ligand acts as a neutral tridentate N2O-donor ligand in both 1 and 2. Two chloride anions remain coordinated to Cu(II) ion in complex 1, but they act as counter ions in complex 2. The catalytic activity of these complexes has been investigated in the oxidation of benzyl alcohol by using H2O2 or TBHP as oxidant. The effects of some influential parameters in catalytic reactions like molar ratio of oxidant-to-substrate, temperature, nature of oxidant and solvent have been studied to obtain the optimum condition. Moreover, the effects of chlorine substituent on the phenyl group (ortho-, meta- and para-positions) has also been explored. The results of these studies show that both 1 and 2 catalyze the oxidation of benzyl alcohol derivatives to the corresponding benzaldehydes and a little amount of the related benzoic acids, produced by over oxidation of benzaldehyde, are also detected in the reaction mixtures. The results indicate that the selectivity and the activity of these catalytic systems depend on the reaction conditions and the steric and electronic properties of the reagents.
Selective oxidation of benzylic alcohols and ethers and oxidative cleavage of benzylic tetrahydropyranyl and trimethylsilyl ethers to their carbonyl compounds by dinitrogen tetroxide-impregnated activated charcoal (N 2O4/charcoal)
Iranpoor, Nasser,Firouzabadi, Habib,Pourali, Ali Reza
, p. 1527 - 1533 (2005)
Benzylic alcohols and ethers were oxidized to their corresponding carbonyl compounds using dinitrogen tetroxide impregnated on activated charcoal (N 2O4/ charcoal) in CH2Cl2 at room temperature. Efficient oxidative cleavage of trimethylsilyl (TMS) and tetrahydropyranyl (THP) ethers to their corresponding carbonyl compounds was also performed by this reagent. High selectivity was observed for oxidation of benzylic alcohols and ethers and also trimethylsilyl ethers in the presence of tetrahydropyranyl ethers. Copyright Taylor & Francis, Inc.
A new application of N-bromosaccharin as a selective and efficient oxidative reagent for regeneration of carbonyl compounds from oximes
Khazaei, Ardeshir,Manesh, Abbas Amini,Rostami, Amin
, p. 2483 - 2486 (2004)
A new method for the direct conversion of various oximes into aldehydes and, ketones by treatment with N-bromosaccharin is described. N-bromosaccharin can be used for an effective, selective and mild oxidizing agent for the regeneration of carbonyl compounds from oximes in good yield.
A highly efficient heterogeneous copper-catalyzed chlorodeboronation of arylboronic acids leading to chlorinated arenes
He, Wen,Zhang, Rongli,Cai, Mingzhong
, p. 764 - 770 (2017)
A highly efficient heterogeneous copper-catalyzed chlorodeboronation of arylboronic acids with inexpensive N-chlorosuccinimide (NCS) was achieved in MeCN in the presence of 10 mol% of l-proline-functionalized MCM-41-immobilized copper(i) complex [MCM-41-l-proline-CuCl] under mild conditions, yielding a variety of aryl chlorides in excellent yields. This method proved to be tolerant of a broad range of functional groups and particularly useful for the conversion of electron-deficient arylboronic acids to aryl chlorides, a transformation that is inefficient without copper catalysis. This heterogeneous copper catalyst can be recovered by a simple filtration of the reaction solution and recycled for at least 10 times without any decreases in activity.
Selective oxidation of benzylic substrates to their corresponding carbonyl compounds with 3,6-Bis(triphenylphosphonium)cyclohexene peroxodisulfate
Badri, Rashid,Soleymani, Mousa
, p. 1325 - 1332 (2003)
3,6-Bis(triphenylphosphonium)cyclohexene peroxodisulfate (BTPCP) was found to be a highly effective and selective oxidant for the conversion of benzyl monohalides, nitrils, and amines to their corresponding carbonyl compounds under mild and neutral conditions.
Aqueous electrosynthesis of carbonyl compounds and the corresponding homoallylic alcohols in a divided cell
Zhang, Li,Zha, Zhenggen,Wang, Zhiyong,Fu, Shengquan
, p. 1426 - 1429 (2010)
An aqueous paired electrosynthesis is studied in a divided cell. On graphite anode Br- was oxidized to Br2 and this generated Br2 oxidized alcohols to the corresponding carbonyl compounds while Sn2+ was reduced
Clean and Selective Oxidation of Alcohols with Oxone and Phase-Transfer Catalysts in Water
An, X. Q.,Kang, M.,Ma, H. C.,Yang, Y. X.,Yang, Z. W.,Zeng, W.
, p. 1790 - 1794 (2020)
Abstract: A new, simple, metal-free, and eco-friendly procedure has been proposed forthe oxidation of alcohols with Oxone (potassium peroxymonosulfate) in water inthe presence of six phase-transfer catalysts (PTC). Phase-transfer catalystswere found to display high catalytic activity in water solution. Furthermore,the oxidation of alcohols was also carried out with relatively good conversionand selectivity in water without any catalyst.
Aerobic oxidation of benzyl- and allylic alcohols under visible light irradiation of a fluorescent lamp in the presence of catalytic iodine
Nakayama, Hiroki,Itoh, Akichika
, p. 1620 - 1621 (2006)
Benzyl alcohols and allylic alcohols were found to be oxidized to the corresponding aldehydes in the presence of a catalytic amount of iodine under irradiation of a fluorescent lamp.
Metabolic and chemical studies on N-(4-chlorobenzyl)-N'-benzoyhydrazine
Kuecuekguezel, S. Gueniz,Kuecuekguezel, Ilkay,Uelgen, Mert
, p. 624 - 630 (2000)
The in vitro hepatic microsomal metabolism of N-(4-chlorobenzyl)-N'-benzoylhydrazine (CBBAH), a model compound representing N-alkyl substituted hydrazides, was studied using hepatic washed rat microsomal preparations fortified with NADPH to identify the possible N-oxidative, N-dealkylated and hydrolytic metabolites. CBBAH and its potential metabolites were prepared, characterized using spectroscopic techniques and then separated using a reversed phase HPLC system with UV detection at 254 nm. CBBAH was chemically converted to the corresponding hydrazone by m-chloroperbenzoic acid (m-CPBA) oxidation. CBBAH was incubated with rat microsomal preparations in the presence of NADPH, extracted into dichloromethane and evaporated finally under nitrogen. The TLC and HPLC results from the metabolic experiments showed that CBBAH produced the corresponding hydrolytic and N-dealkylated metabolites together with the corresponding hydrazone.
Heterogeneous photocatalytic anaerobic oxidation of alcohols to ketones by Pt-mediated hole oxidation
Sun, Danhui,Li, Peihe,Wang, Xia,Wang, Yingying,Wang, Jinghui,Wang, Yin,Lu, Ye,Duan, Limei,Sarina, Sarina,Zhu, Huaiyong,Liu, Jinghai
, p. 11847 - 11850 (2020)
We report a platinum nanocluster/graphitic carbon nitride (Pt/g-C3N4) composite solid catalyst with a photocatalytic anaerobic oxidation function for highly active and selective transformation of alcohols to ketones. The desirable products were successfully obtained in good to excellent yields from various functionalized alcohols at room temperature, including unactivated alcohols. Mechanistic studies indicated that the reaction could proceed through a Pt-mediated hole oxidation initiating an α-alcohol radical intermediate followed by a two-electron oxidation pathway. The merit of this strategy offers a general approach towards green and sustainable organic synthetic chemistry.
