RAS N. D. Zelinsky Institute of Organic Chemistry

Moscow, Russia

RAS N. D. Zelinsky Institute of Organic Chemistry

Moscow, Russia

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Lanxess Deutschland GmbH and RAS N. D. Zelinsky Institute of Organic Chemistry | Date: 2017-01-18

The present invention relates to a process for the reduction of nitrile groups of partially or completely hydrogenated nitrile rubber to amino groups by hydrogenation in the presence of a Raney-cobalt catalyst.

Zalesskiy S.S.,RAS N. D. Zelinsky Institute of Organic Chemistry | Danieli E.,RWTH Aachen | Blumich B.,RWTH Aachen | Ananikov V.P.,Saint Petersburg State University
Chemical Reviews | Year: 2014

The unique feature of the NMR approach is the diversity of chemical and physical properties at different structural levels that can be accessed using a single instrument. The state-of-the-art of modern science brings a number of outstanding research challenges. In the field of chemistry, these include green chemistry procedures, especially cost-efficient and sustainable production of chemicals and pharmaceuticals. Highly efficient, selective, stable, and recyclable catalysts as well as protocols for asymmetric transformations are key requirements for modern catalysis. NMR spectroscopy has been recognized as a valuable tool for promoting research in organic synthesis and catalysis. Another milestone en route to reducing the size of NMR equipment was the improvement of sensitivity obtained with the development of miniature radio frequency coils used to excite and detect the NMR signals of mass-limited samples.

Toukach F.V.,RAS N. D. Zelinsky Institute of Organic Chemistry | Ananikov V.P.,Saint Petersburg State University
Chemical Society Reviews | Year: 2013

All living systems are comprised of four fundamental classes of macromolecules-nucleic acids, proteins, lipids, and carbohydrates (glycans). Glycans play a unique role of joining three principal hierarchical levels of the living world: (1) the molecular level (pathogenic agents and vaccine recognition by the immune system, metabolic pathways involving saccharides that provide cells with energy, and energy accumulation via photosynthesis); (2) the nanoscale level (cell membrane mechanics, structural support of biomolecules, and the glycosylation of macromolecules); (3) the microscale and macroscale levels (polymeric materials, such as cellulose, starch, glycogen, and biomass). NMR spectroscopy is the most powerful research approach for getting insight into the solution structure and function of carbohydrates at all hierarchical levels, from monosaccharides to oligo- and polysaccharides. Recent progress in computational procedures has opened up novel opportunities to reveal the structural information available in the NMR spectra of saccharides and to advance our understanding of the corresponding biochemical processes. The ability to predict the molecular geometry and NMR parameters is crucial for the elucidation of carbohydrate structures. In the present paper, we review the major NMR spectrum simulation techniques with regard to chemical shifts, coupling constants, relaxation rates and nuclear Overhauser effect prediction applied to the three levels of glycomics. Outstanding development in the related fields of genomics and proteomics has clearly shown that it is the advancement of research tools (automated spectrum analysis, structure elucidation, synthesis, sequencing and amplification) that drives the large challenges in modern science. Combining NMR spectroscopy and the computational analysis of structural information encoded in the NMR spectra reveals a way to the automated elucidation of the structure of carbohydrates. This journal is © The Royal Society of Chemistry 2013.

Egorova K.S.,RAS N. D. Zelinsky Institute of Organic Chemistry | Ananikov V.P.,Saint Petersburg State University
ChemSusChem | Year: 2014

Rapid progress in the field of ionic liquids in recent decades led to the development of many outstanding energy-conversion processes, catalytic systems, synthetic procedures, and important practical applications. Task-specific optimization emerged as a sharpening stone for the fine-tuning of structure of ionic liquids, which resulted in unprecedented efficiency at the molecular level. Ionic-liquid systems showed promising opportunities in the development of green and sustainable technologies; however, the chemical nature of ionic liquids is not intrinsically green. Many ionic liquids were found to be toxic or even highly toxic towards cells and living organisms. In this Review, we show that biological activity and cytotoxicity of ionic liquids dramatically depend on the nature of a biological system. An ionic liquid may be not toxic for particular cells or organisms, but may demonstrate high toxicity towards another target present in the environment. Thus, a careful selection of biological activity data is a must for the correct assessment of chemical technologies involving ionic liquids. In addition to the direct biological activity (immediate response), several indirect effects and aftereffects are of primary importance. The following principal factors were revealed to modulate toxicity of ionic liquids: i)?length of an alkyl chain in the cation; ii)?degree of functionalization in the side chain of the cation; iii)?anion nature; iv)?cation nature; and v)?mutual influence of anion and cation. Copyright © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Tabolin A.A.,RAS N. D. Zelinsky Institute of Organic Chemistry | Ioffe S.L.,RAS N. D. Zelinsky Institute of Organic Chemistry
Chemical Reviews | Year: 2014

Hydroxylamines and their derivatives have found a wide range of applications in organic synthesis. Some relevant examples of the application of N-oxyenamine rearrangements to organic synthesis have already been described in reviews such as the one devoted to the Trofimov pyrrole synthesis or the Bartoli indole synthesis. In such cases, in order to avoid repetition, we confine our discussion in this review to some general remarks. The exocyclic double bond selectively formed in the E configuration. The stereochemistry of the dipolarophile selectively transferred into the product, whereas the selectivity of the C5-stereocenter varied with solvent choice. This prevents nitrogen addition to the carbonyl group and at the same time increases the nucleophilicity of the oxygen atom. For introduction of the O-vinyl moiety into a hydroxylamine molecule a Michael addition is used.

Ananikov V.P.,RAS N. D. Zelinsky Institute of Organic Chemistry
Chemical Reviews | Year: 2011

Recent development has shown that ionic liquids (IL) have emerged as very attractive media for performing chemical reactions with a well-established potential in the context of Green Chemical synthesis. Despite the ongoing wide interest in ILs, some important unanswered questions remain regarding the mechanisms of chemical reactions in ILs, catalyst stability and decomposition pathways, and the nature of the solvent-solute interactions. Relaxation measurements are another source of valuable information about the structure and dynamics of ILs. The NMR study suggested that an IL surrounding interacts more strongly with the chloride ion than with the hydrogen dichloride ion compared to the other solvents studied. Gas solubility is a very important property related to the performance of several catalytic reactions of industrial importance.

Ananikov V.P.,RAS N. D. Zelinsky Institute of Organic Chemistry | Beletskaya I.P.,Moscow State University
Organometallics | Year: 2012

The current state of the art and perspectives of homogeneous and heterogeneous catalysis are discussed for C-C and C-heteroatom bond formation in organic synthesis. The relationship between catalyst centers represented by a single metal atom and by multiple metal atoms is considered for reactions taking place in solution. The influence of leaching and catalyst evolution in the liquid phase on the activity, selectivity, and stability of the catalyst is highlighted from a mechanistic point of view. Metal nanoparticle and "nanosalt" types of catalysts are compared for constructing new C-C and C-heteroatom bonds. © 2012 American Chemical Society.

Toukach P.V.,RAS N. D. Zelinsky Institute of Organic Chemistry
Journal of Chemical Information and Modeling | Year: 2011

Bacterial carbohydrate structure database (BCSDB) is an open-access project that collects primary publication data on carbohydrate structures originating from bacteria, their biological properties, bibliographic and taxonomic annotations, NMR spectra, etc. Almost complete coverage and outstanding data consistency are achieved. BCSDB version 3 and the principles lying behind it, including glycan description language, are reported. © 2011 American Chemical Society.

Beletskaya I.P.,Moscow State University | Ananikov V.P.,RAS N. D. Zelinsky Institute of Organic Chemistry
Chemical Reviews | Year: 2011

The state-of-the-art development of C-S, C-Se, and C-Te bond-formation research involving cross-coupling and addition reactions, are discussed. In 1998, after screening the available ligands, Zheng and coworkers found that Pd(OAc)2-BINAP-LiCl and in particular the Pd(OAc)2-Tol- BINAP system can catalyze cross-coupling reactions of various triflates. Krief and coworkers showed that NaH or CsOH can be a more convenient choice, although the reaction may require higher temperatures. Venkataraman and co-workers suggested using neocuproin as a ligand significantly extending the scope of the reaction to include aryl(hetaryl) iodides with both electron-donating and electron-accepting substituents as well as various alkyl and aryl thiols. Wang, Wu, and co-workers reported an excellent mechanistic study of a methylacetylene bisselenation on a Pd catalyst using theoretical calculations at the B3LYP level.

Sukhorukov A.Y.,RAS N. D. Zelinsky Institute of Organic Chemistry | Ioffe S.L.,RAS N. D. Zelinsky Institute of Organic Chemistry
Chemical Reviews | Year: 2011

Six-membered cyclic oxime ether (SCOE) has been studied as a valuable intermediates for directed organic synthesis. Four general approaches to the synthesis of SCOE are known, [4 + 2]-cycloaddition reactions of heterodienes with the fragment CdC-NdO to olefins, intramolecular cyclization of γ-functionalized oximes, an intramolecular cyclization of functionalized O-substituted hydroxylamines, and transformations of the N-O-containing heterocyclic compounds. The most common approach to the synthesis of SCOE 1 is the [4+2]-cycloaddition of conjugated nitrosoalkenes 3 to olefins 4. Since most nitrosoalkenes 3 are highly reactive species, they are usually generated in situ from the corresponding R-halooximes 5 upon the action of a base. A large group of methods for the preparation of SCOE 1 and 2 is based on intramolecular cyclization of oximes bearing an electrophilic center at the γ-position.

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