61040-96-8Relevant academic research and scientific papers
Regioselective Hydroperoxylation of Aziridines and Epoxides Only with Aqueous Hydrogen Peroxide
Saleh, SK Abu,Hazra, Atanu,Hajra, Saumen
, p. 391 - 404 (2021/11/01)
A catalyst and organic solvent-free regioselective hydroperoxylation of aziridines and epoxides, including spiroaziridine- and spiroepoxy oxindoles have been explored with commercially available 50% aq. H2O2. This method provides an access to secondary benzylic β-hydroperoxy amines and -alcohols and tertiary 3-hydroperoxy oxindoles. The protocol is also applicable to the less reactive alkyl aziridines. Furthermore, an acid-catalyzed Kornblum-DeLaMare type rearrangement of secondary benzylic hydroperoxide has also been revealed to afford amino- and hydroxyl ketones. (Figure presented.).
Magnetic nano-graphene oxide-supported molybdenum (Fe3O4/GO-Mo) as a green, efficient, and recyclable catalyst for synthesis of β-hydroxy hydroperoxides
Liu, Yu-Heng,Hu, Hai-Chuan,Ma, Zi-Chuan,Dong, Yan-Fei,Wang, Can,Pang, Yun-Meng
, p. 551 - 556 (2018/03/27)
Abstract: Magnetic nano-graphene oxide-supported molybdenum was readily prepared and identified as an efficient and recyclable catalyst for ring opening of various epoxides with ethereal hydrogen peroxide. The reaction proceeded under mild conditions to g
Aerobic Photooxidative Synthesis of β-Alkoxy Monohydroperoxides Using an Organo Photoredox Catalyst Controlled by a Base
Asano, Yuya,Nagasawa, Yoshitomo,Yamaguchi, Eiji,Itoh, Akichika
supporting information, p. 409 - 412 (2018/02/21)
Transition-metal-free synthesis of β-alkoxy monohydroperoxides via aerobic photooxidation using an acridinium photocatalyst was developed. This method enables the synthesis of some novel hydroperoxides. The peroxide source is molecular oxygen, which is cost-effective and atomically efficient. Magnesium oxide plays an important role as a base in the catalytic system.
Magnetic nanoparticles (CoFe2O4)-supported phosphomolybdate as an efficient, green, recyclable catalyst for synthesis of b-hydroxy hydroperoxides
Li, Pei-He,Li, Bao-Le,An, Zhi-Min,Mo, Li-Ping,Cui, Zhen-Shui,Zhang, Zhan-Hui
, p. 2952 - 2959 (2014/03/21)
Magnetic nanoparticles (CoFe2O4)-sup-ported phosphomolybdate ([CoFe2O4@SiO2-PrNH 2-PMo]) was readily prepared and identified as an effi-cient catalyst for ring-opening of various epoxides w
Efficient conversion of epoxides into β-hydroperoxy alcohols catalyzed by antimony trichloride/SiO2
Liu, Yu-Heng,Zhang, Zhan-Hui,Li, Tong-Shuang
experimental part, p. 3314 - 3318 (2009/05/07)
Efficient ring-opening of various epoxides with hydrogen peroxide, catalyzed by antimony trichloride/SiO2, afforded the corresponding β-hydroperoxy alcohols in good to excellent yields under mild reaction conditions. The reactions were efficien
Efficient oxidative cleavage of olefins to carboxylic acids with hydrogen peroxide catalyzed by methyltrioctylammonium tetrakis(oxodiperoxotungsto)phosphate(3-) under two-phase conditions. Synthetic aspects and investigation of the reaction course
Antonelli, Ermanno,D'Aloisio, Rino,Gambaro, Mario,Fiorani, Tiziana,Venturello, Carlo
, p. 7190 - 7206 (2007/10/03)
The oxidative cleavage of alkenes to carboxylic acids with 40% w/v aqueous hydrogen peroxide catalyzed by methyltrioctylammonium tetrakis(oxodiperoxotungsto)phosphate(3-) (1a) is reported to occur in high yields and selectivities under two-phase conditions in the absence of organic solvents. On the basis of a study of the reaction, two main reaction pathways leading to acids have been recognized, the first one involving the perhydrolysis and the second one the hydrolysis of the epoxide initially formed. The "perhydrolytic" reaction pathway appears to play a primary role in the oxidation of medium- and long-chain alkenes to acids, while it intervenes to a rather limited extent in the oxidation of arylalkenes and C5-C7 cycloalkenes. The occurrence of this pathway has been proved by the isolation of the intermediate β-hydroperoxy alcohols and their transformation into acids with H2O2 and la. The course of this transformation, involving an initial oxidation (to α-oxo hydroperoxide) or decomposition (to carbonyl compounds) of the β-hydroperoxy alcohol intermediate, is described. The primary oxidation products, α-hydroperoxy ketones, have been isolated in the case of internal β-hydroperoxy alcohols, whereas their presence has been evidenced with terminal β-hydroperoxy alcohols bearing a secondary hydroxy group. Hydrogen peroxide concentration appears to exert a remarkable influence on medium acidity, and its effects on the reaction efficiency are shown.
Titanium-Catalyzed Diastereoselective Epoxidations of Ene Diols and Allylic Alcohols with β-Hydroperoxy Alcohols as Novel Oxygen Donors
Adam, Waldemar,Peters, Karl,Renz, Michael
, p. 3183 - 3189 (2007/10/03)
β-Hydroperoxy alcohols 1-4 serve as effective tridentate oxygen donors for the highly diastereo-selective, titanium-catalyzed epoxidation of ene diols 5a-e. Thus, in contrast to the bidentate tert-butyl hydroperoxide, the usual oxygen donor employed in Sharpless-type epoxidations and known to work poorly for polyhydroxy substrates, the tridentate β-hydroperoxy alcohols efficiently replace the tridentate epoxy diol products 6a-e in the titanium template and thereby the catalytic cycle is sustained by replenishing with efficacy the loaded complex necessary for the oxygen transfer. Irrespective of the substitution pattern of the double bond or the configuration (erythro versus threo) of the diol functionalities in the ene diol substrate, high diastereoselectivities are observed for the epoxy diol products. The high stereochemical control is due to the rigid transition state for the oxygen transfer, which is imposed by the multiple titanium-oxygen bonding and coordination in the titanium template. The observed erythro selectivity for the ene diol derives from the additional bonding of its homoallylic hydroxy group to the titanium center, which fixes the substrate conformation in such a way that the oxygen atom to be transferred approaches from the side of the allylic oxygen functionality (cf. loaded complex A). This additional binding of the bidentate ene diol in the titanium template is also manifested in the enhanced reactivity of the ene diol versus the monodentate allylic alcohols. Nevertheless, the less reactive allylic alcohols also display a high erythro selectivity, provided these monodentate substrates possess 1,2-allylic strain. For the first time a direct, diastereoselective, and catalytic epoxidation of ene diols has been made available for synthetic applications, without recourse to protection group methodology.
