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Tatiana O. Krylova

Bio: Tatiana O. Krylova is an academic researcher from A. N. Nesmeyanov Institute of Organoelement Compounds. The author has contributed to research in topics: Nucleophile & Triethylsilane. The author has an hindex of 1, co-authored 1 publications receiving 12 citations.

Papers
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Journal ArticleDOI
TL;DR: Several types of addition reactions to the CC bond of alkyl 2-cyanoacrylates, CH2C(CN)COOR (1), are considered in this article.
Abstract: Several types of addition reactions to the CC bond of alkyl 2-cyanoacrylates, CH2C(CN)COOR (1), are considered. The first examples deal with addition of CH-Acids (pKa less than 13) and of H2S in the presence of catalytic amounts of strong amines, also of mercaptans, thiocarboxylic, and thiophosphoric acids. P-Sulfenylchlorides and acidic phosphites add irreversibly at 20°C to form addition products in accordance with the distribution of charges in 1. HCl reversibly adds to 1 and to the acid chloride CH2C(CN)COCl (2). Alcohols and H2O also add reversibly to the acid CH2C(CN)COOH (3) and to esters of 1 to transform 1 and 3 into polymers. Triethylsilane in the presence of CF3COOH (4) reduces the CC bond of 1 and 3 to the corresponding saturated derivatives. The second set of examples involves reactions of 1 with P-III compounds in the presence or absence of 4. Ph3P as well as other weak nucleophiles reversibly add to 1 in the absence of 4 to cause instant polymerization. However, 4 protonates an initially formed zwitter-ion in the reaction of 1 with Ph3P,(EtO)2PCl,Ph2PCl and thiourea to afford stable addition products. IR spectroscopy reveals the formation of H-complexes of 4 with the CN and COOR groups of 1, which stimulates the addition of the weak nucleophile (o-C6H4O2)PCl to the CC bond of 1. This reagent does not react with 1 in the absence of 4. Strong nucleophiles, Alk3P, and (Et2N)3P in excess irreversibly add at 20°C to 1 to form zwitterions, which specifically react with PhNCO to give stable products. 1,3,2-Dioxaphospholes react with 1 either to form spirophosphoranes or 2-cyano-3-phosphoranylpropionates.

12 citations


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Patent
10 Dec 2010
TL;DR: In this paper, an oil of lubricating viscosity and a compound obtained/obtainable by a process comprising reacting a glycolic acid, a 2-halo-acetic acid or a lactic acid, or an alkali or alkaline metal salts thereof with at least one member selected from the group consisting of an amine, an alcohol, and an amino alcohol.
Abstract: The invention provides a lubricating composition containing an oil of lubricating viscosity and a compound obtained/obtainable by a process comprising reacting a glycolic acid, a 2-halo-acetic acid, or a lactic acid, or an alkali or alkaline metal salts thereof, (typically glycolic acid or a 2-halo-acetic acid) with at least one member selected from the group consisting of an amine, an alcohol, and an aminoalcohol. The invention further relates to the use of the lubricating composition in an internal combustion engine.

60 citations

Journal ArticleDOI
TL;DR: In this review article, after a general description of monomer and polymer properties, radical homo- and copolymerization studies are described, along with an overview of nanoparticle preparations.
Abstract: Cyanoacrylates (CAs) are well-known fast-setting adhesives, which are sold as liquids in the presence of stabilizers. Rapid anionic polymerization on exposure to surface moisture is responsible for instant adhesion. The more difficult, but synthetically more useful radical polymerization is only possible under acidic conditions. Recommendations on the handling of CAs and the resulting polymers are provided herein. In this review article, after a general description of monomer and polymer properties, radical homo- and copolymerization studies are described, along with an overview of nanoparticle preparations. A summary of our recently reported radical polymerization of CAs, using reversible addition-fragmentation chain transfer (RAFT) polymerization, is provided.

33 citations

Journal ArticleDOI
TL;DR: Triisopropylphosphine reacts with 2-cyanoacrylates with formation of the P-zwitterionic species 2a and 2b.
Abstract: Triisopropylphosphine reacts with 2-cyanoacrylates with formation of the P-zwitterionic species 2a and 2b. The reaction of 2b with trimethylsilyltriflate, in the presence of traces of water, leads to the phosphonium triflate 3. 2b is alkylated at the carbon atom with methyl iodide with formation of the phosphonium iodide 4. The initially formed adducts of the zwitterionic species 2a and 2b with tosyl azide and with tosyl isocyanate are thermodynamically unstable. In the first case, the final products of the reaction are tosyl iminotriisopropylphosphine imide 6 and 2-cyanoacrylate polymers. In the second case, the reaction leads to the zwitterionic product 8, and, in the presence of traces of water, to the molecular complexes 9a and 9b. The reaction of the zwitterionic species 2a and 2b with methylisocyanate proceeds in an unusual way, resulting in the formation of the zwitterionic species 12a and 12b, as a result of the insertion of methylisocyanate into the C[sbnd]C bond of the starting zwitteri...

18 citations

Journal ArticleDOI
TL;DR: In this article, the use of alkyl 2-cyanoacrylates in organic synthesis, in polymers and in the chemistry of adhesives is described.
Abstract: Methods for the synthesis, properties and applications of alkyl 2-cyanoacrylates are surveyed. The reactions of alkyl 2-cyanoacrylates with various nucleophiles (thiols, alcohols, diols, hydrogen sulfide, phosphines, etc.) including a new reaction involving insertion of isocyanates and isothiocyanates into the C=C bonds in the adducts of alkyl 2-cyanoacrylates with trialkylphosphines are considered. The prospects for the use of alkyl 2-cyanoacrylates in organic synthesis, in the chemistry of polymers and in the chemistry of adhesives are described. The bibliography includes 117 references.

18 citations

Journal ArticleDOI
TL;DR: I-Adamantylmethyl 2-cyanoacryloyl chloride with 1-adamantylmethanol was synthesized by transesterification of methyl 2-cyanacrylate with 1,10-decanediol as discussed by the authors.
Abstract: I-Adamantylmethyl 2-cyanoacrylate (1) was prepared by the reaction of 2-cyanoacryloyl chloride with 1-adamantylmethanol . 1,10-Decanediol bis-2-cyanoacrylate (2) was synthesized by transesterification of methyl 2-cyanoacrylate with 1,10-decanediol. Esters1 and2 were studied by X-ray structural analysis.

10 citations