Marina A. Taranova

Lomonosov Moscow State University

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E. D. Matveeva

Lomonosov Moscow State University

Rolf Gleiter

Heidelberg University

НС

Н. С. Зефиров

Institute of Physiologically Active Compounds

Tatyana A. Podrugina

Lomonosov Moscow State University

A. A. BORISENKO

Geotek (United Kingdom)

T. A. Podrugina

Lomonosov Moscow State University

T. D. Nekipelova

Institute of Biochemical Physics NM Emanuel

АВ

А. В. Миронов

Lomonosov Moscow State University

V. A. Kuz’min

Institute of Biochemical Physics NM Emanuel

N. S. Zefirov

Moscow State University

Cooperative Institutions

Lomonosov Moscow State University

Moscow State University

Russian Academy of Sciences

Institute of Physiologically Active Compounds

N.D. Zelinsky Institute of Organic Chemistry

State Research Institute of Organic Chemistry and Technology

Institute of Biochemical Physics NM Emanuel

Weatherford College

North Ossetian State University

Nova Institut

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ChemInform Abstract: Phosphonium‐Iodonium Ylides with Heteroatomic Groups in the Synthesis of Anellated P‐Containing Heterocycles.

ChemInform (2014)

E. D. Matveeva Tatyana A. Podrugina Marina A. Taranova Dimitry S. Vinogradov Rolf Gleiter

10.1002/chin.201422191

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Citations (0)

Phosphonium-Iodonium Ylides with Heteroatomic Groups in the Synthesis of Annelated P-Containing Heterocycles

The Journal of Organic Chemistry (2013)

E. D. Matveeva Tatyana A. Podrugina Marina A. Taranova D. S. Vinogradov Rolf Gleiter

The preparation and chemistry of novel sulfonyl- and phosphoryl-derived λ(3)-iodanes are reported. These compounds with three different heteroatoms attached to a negatively charged C atom represent potentially useful reagents that combine in one molecule the synthetic advantages of a phosphonium ylide and an iodonium salt. Specifically, they can react with a number of acetylenes, leading to hitherto unknown sulfonyl- and phosphoryl-substituted phosphinolines, phosphininothiophenes, and a novel type of annelated P-containing heterocycle--phosphininopyrazole.

Phosphonium

Ylide

Heteroatom

Sulfonyl

Phosphonium salt

10.1021/jo401514d

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Citations (23)

Mechanism and remarkable features of photoinduced cycloaddition of phenylacetylene to mixed phosphonium-iodonium ylide

Doklady Chemistry (2012)

T. D. Nekipelova Marina A. Taranova E. D. Matveeva T. A. Podrugina V. A. Kuz’min

Phenylacetylene

Ylide

Phosphonium

10.1134/s0012500812110092

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Citations (11)

Photocyclization of a mixed phosphonium-iodonium ylide with phenylacetylene: A formal kinetic approach to the mechanistic study

Kinetics and Catalysis (2015)

T. D. Nekipelova Marina A. Taranova E. D. Matveeva V. A. Kuz’min Н. С. Зефиров

Ylide

Phosphonium

Phenylacetylene

Induction period

Trifluoroacetic acid

10.1134/s0023158415040138

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Citations (6)

CCDC 888582: Experimental Crystal Structure Determination

The Cambridge Structural Database (2013)

E. D. Matveeva Marina A. Taranova T. A. Podrugina Rolf Gleiter Н. С. Зефиров

An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.

10.5517/ccytmy9

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Photochemical Synthesis of Phosphinolines from Phosphonium−Iodonium Ylides

The Journal of Organic Chemistry (2010)

E. D. Matveeva Tatyana A. Podrugina Marina A. Taranova A. A. BORISENKO А. В. Миронов

We describe three different series of experiments which were undertaken to test our hypothesis that during irradiation of phosphonium-iodonium ylides (1a, 1b) an electrophilic carbene is generated. By opposing the assumed intermediate to monosubstituted alkynes, we observed in the case of electron-rich substituents at the triple bond a domination of a 1,3-dipolar cycloaddition of the intermediate with the triple bond to yield furans. In the case of electron poorer substituents, the formation of phosphinolines prevails. A second series of experiments was carried out with mixed ylides in which one phenyl ring at the triarylphosphonium group was replaced by a thienyl group. In this case, we observe only an intramolecular reaction with the thienyl ring to yield the phosphinolines 21-23. In a third test, we replaced in the mixed ylides 1a, 1b the COR group by a CN substituent. This modification leads to phosphinolines only and avoids a 1,3-dipolar cycloaddition.

Phosphonium

Triple bond

10.1021/jo101993a

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Citations (39)

ChemInform Abstract: Photochemical Synthesis of Phosphinolines from Phosphonium—Iodonium Ylides.

ChemInform (2011)

E. D. Matveeva Tatyana A. Podrugina Marina A. Taranova A. A. BORISENKO А. В. Миронов

Abstract Irradiation of phosphonium—iodonium ylides with terminal alkynes results in formation of phosphinolines and/or 1,3‐cycloaddition products depending on the nature of ylide and alkyne substituents.

Phosphonium

10.1002/chin.201116189

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Citations (0)

Annelated P-containing heterocycles from aryl- and hetaryl-substituted phosphonium iodonium ylides with a methoxycarbonyl-group

Tetrahedron (2013)

E. D. Matveeva Tatyana A. Podrugina Marina A. Taranova Ekaterina Y. Melikhova Rolf Gleiter

Phosphonium

Ylide

10.1016/j.tet.2013.06.066

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Citations (18)

CCDC 843537: Experimental Crystal Structure Determination

The Cambridge Structural Database (2011)

E. D. Matveeva T. A. Podrugina Marina A. Taranova A. A. BORISENKO Andrei V. Mironov

10.5517/ccx9rwt

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ChemInform Abstract: Hetaryl‐Substituted Phosphonium‐Iodonium Ylides in Synthesis of Heterocycles.

ChemInform (2012)

E. D. Matveeva Tatyana A. Podrugina Marina A. Taranova Anastasiya M. Ivanova Rolf Gleiter

Abstract Depending on the aryl moiety of the arylcetylenes and the heteroaryl group at the phosphonium group, the reaction of new ylides (I) and (VII) with arylacetylenes affords selectively phosphininofurans, furans, or a benzo‐fused phosphinoline.

Phosphonium

Moiety

10.1002/chin.201244186

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