96839-90-6Relevant academic research and scientific papers
Development of new recyclable reagents and catalytic systems based on hypervalent iodine compounds
Yusubov, Mekhman S.,Zhdankin, Viktor V.
experimental part, p. 185 - 191 (2011/03/19)
Recent advances in the development of polymer-supported iodine(V) oxidants, recyclable monomeric hypervalent iodine(III) reagents and catalytic systems based on hypervalent iodine compounds are discussed. These efficient and environmentally friendly reagents and catalysts are particularly useful for oxidative transformations of alcohols to carbonyl compounds and for oxidations at the benzylic position.
Preparation and X-ray crystal structure of 2-iodyl-N,N-dialkylaniline oxides: First entry into the heterocyclic system of benziodoxazole
Zhdankin, Viktor V.,Nemykin, Victor N.,Karimov, Rashad R.,Kazhkenov, Zeinul-Gabiden
supporting information; experimental part, p. 6131 - 6133 (2009/05/06)
The oxidation of 2-iodo-N,N-dialkylanilines with an excess of dimethyldioxirane in acetone affords 2-iodyl-N,N-dialkylaniline oxides, structural features of which are in agreement with the new heterocyclic system of benziodoxazole. The Royal Society of Chemistry.
Preparation and reactivity of polymer-supported 2-iodylphenol ethers, an efficient recyclable oxidizing system
Karimov, Rashad R.,Kazhkenov, Zeinul-Gabiden M.,Modjewski, Matthew J.,Peterson, Eric M.,Zhdankin, Viktor V.
, p. 8149 - 8151 (2008/02/13)
(Chemical Equation Presented) Preparation of new recyclable polymer-supported oxidizing reagents based on 2-iodylphenol ethers is described. The synthesis employs commercially available aminomethylated polystyrene or Merrifield resin and affords polymer-supported 2-iodylphenol ethers with loading up to 0.86 mmol/g with respect to IO2 groups. The new reagents effect clean and efficient conversion of a wide range of alcohols, including heteroatomic and unsaturated structures, to the corresponding carbonyl compounds. Recycling of the resins is possible with minimal loss of activity after several reoxidations.
Facile preparation and reactivity of polymer-supported N-(2-lodyl-phenyl)- acylamide, an Efficient Oxidizing System
Ladziata, Uladzimir,Willging, Jeff,Zhdankin, Viktor V.
, p. 167 - 170 (2007/10/03)
(Chemical Equation Presented) A simple three-step preparation of polymer-supported N-(2-iodyl-phenyl)-acylamide (NIPA resin) starting from 2-iodoaniline is described. The resin was obtained with good loading levels (0.7-0.8 mmol g-1) and has been successfully used for efficient oxidation of a diverse collection of alcohols. Thus, treating alcohols with 1.0 equiv of the resin in 1,2-dichloroethane under reflux for 30-60 min allowed rapid and in most cases complete conversion to the corresponding carbonyl compound.
Highly efficient RuCl3-catalyzed disproportionation of (diacetoxyiodo)benzene to iodylbenzene and iodobenzene; leading to the efficient oxidation of alcohols to carbonyl compounds
Yusubov, Mekhman S.,Chi, Ki-Whan,Park, Joo Yeon,Karimov, Rashad,Zhdankin, Viktor V.
, p. 6305 - 6308 (2007/10/03)
(Diacetoxyiodo)benzene (DIB) selectively oxidizes primary and secondary alcohols to the respective carbonyl compounds in the presence of RuCl3 (0.8-1.0 mol %) at room temperature in aqueous acetonitrile. This reaction proceeds via an initial instantaneous Ru-catalyzed disproportionation of DIB to iodobenzene and iodylbenzene with the latter acting as the actual stoichiometric oxidant toward alcohols.
2-Iodylphenol ethers: Preparation, X-ray crystal structure, and reactivity of new hypervalent iodine(V) oxidizing reagents
Koposov, Alexey Y.,Karimov, Rashad R.,Geraskin, Ivan M.,Nemykin, Victor N.,Zhdankin, Viktor V.
, p. 8452 - 8458 (2007/10/03)
2-Iodylphenol ethers were prepared by the dimethyldioxirane oxidation of the corresponding 2-iodophenol ethers and isolated as chemically stable, microcrystalline products. Single-crystal X-ray diffraction analysis of 1-iodyl-2-isopropoxybenzene 8c and 1-iodyl-2-butoxybenzene 8d revealed pseudopolymeric arrangements in the solid state formed by intermolecular interactions between IO2 groups of different molecules. 2-Iodylphenol ethers can selectively oxidize sulfides to sulfoxides and alcohols to the respective aldehydes or ketones.
Modulation of the reactivity profile of IBX by ligand complexation: Ambient temperature dehydrogenation of aldehydes and ketones to α,β-unsaturated carbonyl compounds
Nicolaou,Montagnon, Tamsyn,Baran, Phil S.
, p. 993 - 996 (2007/10/03)
The reactivity profile of IBX can be altered by complexation with various ligands (e. g. 1-4). A new complex, IBX·MPO, is a remarkably effective oxidant and allows the room-temperature dehydrogenation of carbonyl compounds, for example, the formation of cyclooctenones 6 and 7 from cyclooctanone 5. IBX = iodoxybenzoic acid; MPO = 4-methoxypyridine-N-oxide.
Synthesis and Reaction of (3-Phenylseleno-1-alkenyl)triphenylphosphonium Salts
Minami, Toru,Nakayama, Minoru,Nakamura, Taku,Okada, Yoshiharu
, p. 1741 - 1742 (2007/10/02)
The reaction of allylic triphenylphosphonium ylides with benzeneselenenyl bromide gave (3-phenylseleno-1-alkenyl)triphenylphosphonium salts in good yields.Oxidation of the salts produced α,β-unsaturated aldehydes.
BICHROMATES DE PHOSPHONIUM: REACTIFS D'OXYDATION
Cristau, Henri-Jean,Torreilles, Eliane,Morand, Philippe,Christol, Henri
, p. 1775 - 1776 (2007/10/02)
The bisphosphonium bichromate 1, appears as particularly mild and selective for the oxidation of primary or secondary alcohols.It performs the oxidation of primary alcohols into aldehydes without further oxidation in acid and without double-bond isomerisation or migration for such alcohols as geraniol; it allows also the fully selective oxidation of benzylic or allylic alcohols versus aliphatic alcohols.
