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V F Mironov - One of the best experts on this subject based on the ideXlab platform.
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synthesis crystal structure and hydrolysis of novel isomeric cage p c p o phosphoranes on the basis of 4 4 5 5 tetramethyl 2 2 oxo 1 2 diphenylethoxy 1 3 2 dioxaphospholane and Hexafluoroacetone
RSC Advances, 2016Co-Authors: N R Khasiyatullina, Dmitry B. Krivolapov, V F Mironov, E V Mironova, O I GnezdilovAbstract:The reaction of 4,4,5,5-tetramethyl-2-(2-oxo-1,2-diphenylethoxy)-1,3,2-dioxaphospholane with Hexafluoroacetone leads to the simultaneous formation of regioisomeric cage (P–C/P–O)-phosphoranes, the structures of which are unequivocally confirmed by XRD. The rearrangement of the P–C-isomer to P–O-isomer with high stereoselectivity (>96%) takes place in methylene chloride solution with the retention of the phosphorus coordination. It was found that the stepwise hydrolysis of the P–O-isomer initially gives 2-(2,3-dihydroxy-1,2-diphenyl-3-trifluoromethyl-4,4,4-trifluorobutyloxy)-4,4,5,5-tetramethyl-2-oxo-1,3,2-dioxaphospholane as the only stereoisomer whose structure is also confirmed by XRD. Further hydrolysis of this compound leads to the formation of 2,3-dihydroxy-3-trifluoromethyl-4,4,4-trifluoro-1,2-diphenylbutylphosphate and pinacol, which forms the solvate in the crystal. Hydrolysis of the P–C-isomer yields 2-hydroxy-4,4,5,5-tetramethyl-2-oxo-1,3,2-dioxaphospholane, benzoin and hexafluoroisopropanol.
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stereoselective pco poc rearrangement of p c cage phosphorane in the reaction of 4 5 dimethyl 2 2 oxo 1 2 diphenyl ethoxy 1 3 2 dioxaphospholane with Hexafluoroacetone
Journal of Organic Chemistry, 2016Co-Authors: V F Mironov, Mudaris N. Dimukhametov, Sergey V. Efimov, Roza M. Aminova, Farida Kh. Karataeva, Dmitry B. Krivolapov, Ekaterina V. Mironova, Vladimir V. KlochkovAbstract:Interaction of 4,5-dimethyl-2-(2-oxo-1,2-diphenyl)ethoxy-1,3,2-dioxaphospholane, bearing a carboxyl group in the γ-position with respect to the phosphorus atom and obtained from d,l-butanediol, with Hexafluoroacetone (CCl4, −40 °C) leads to the simultaneous formation of regio- and stereoisomeric cage-like phosphoranes with phosphorus–carbon and phosphorus–oxygen bonds with a high stereoselectivity (>95%), whose structure was determined by 1D and 2D NMR spectroscopy and XRD. When stored as a solution in dichloromethane for one month, the PCO-isomer rearranges into the thermodynamically more stable POC-isomer of the cage-like phosphorane. Mild hydrolysis of the PCO/POC-isomers proceeds with a high chemoselectivity and leads to the formation of P(IV)-dioxaphospholane derivatives. Acidic hydrolysis of the POC-isomer leads to the formation of an oxirane derivative with an unexpectedly high stereoselectivity (>95%). DFT calculations (using the PBE functional) allowed us to obtain structures and energies of the ...
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reaction of 4 5 dimethyl 2 2 oxo 1 2 diphenylethoxy 1 3 2 dioxaphospholane with Hexafluoroacetone formation of isomeric caged phosphoranes with phosphorus carbon and phosphorus oxygen bonds
Russian Chemical Bulletin, 2015Co-Authors: V F Mironov, Mudaris N. Dimukhametov, S V Efimov, Kh F Karataeva, V V KlochkovAbstract:4,5-Dimethyl-2-(2-oxo-1,2-diphenylethoxy)-1,3,2-dioxaphospholane bearing the carbonyl group at the γ-position to the phosphorus atom reacted with Hexafluoroacetone to give regio- and stereoisomeric caged phosphoranes with phosphorus–carbon and phosphorus–oxygen bonds.
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reactions of 2 5 methyl 2 phenyl 2h 1 2 3 diazaphosphol 4 yl 4h 1 3 2 benzodioxaphosphinin 4 one with chloral and Hexafluoroacetone
Mendeleev Communications, 2011Co-Authors: Dmitry B. Krivolapov, V F Mironov, L M Abdrakhmanova, G A Ivkova, E V Mironova, I V KonovalovaAbstract:Abstract Reaction of 2-(5-methyl-2-phenyl-2H-1,2,3-diazaphosphol-4-yl)-4H-1,3,2-benzodioxaphosphinin-4-one with chloral occurs at Piii atom of the 1,3,2-dioxaphosphinine cycle giving mostly 2-chlorocarbonylphenyl 2,2-dichlorovinyl (5-methyl-2-phenyl-2H-1,2,3-diazaphosphol-4-yl)phosphonate, whereas Hexafluoroacetone incorporates into the 1,3,2-dioxaphosphorine cycle affording the corresponding 1,3,2-benzodioxaphosphepine.
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an unusual cascade reaction of 4 5 dihydro 4 4 bis trifluoromethyl 2 phenyl 6 7 4 chlorobenzo e 1 3 2 dioxaphosphepin 5 one with chloral
Mendeleev Communications, 2010Co-Authors: V F Mironov, Yuliya Yu Borisova, L M Burnaeva, I A Litvinov, V V Zverev, R Z Musin, I V KonovalovaAbstract:The reaction of 4,5-dihydro-4,4-bis(trifluoromethyl)-2-phenyl-6,7-(4-chlorobenzo)[e]-1,3,2-dioxaphosphepin-5-one with chloral (1:2) proceeds with evolving Hexafluoroacetone and gives spiro{2-oxo-4-trichloromethyl-4,5-dihydro-2-phenyl-6,7-(4-chlorobenzo)[f]-1,3,2-dioxaphosphepine-5,2’-(3’-trichloromethyl)oxirane} with a high stereoselectivity. Configuration of the four chiral centres (P2SC4SC5SC3'S /P2RC4RC5RC3’R) was determined by a single crystal X-ray diffraction.
Dmitry B. Krivolapov - One of the best experts on this subject based on the ideXlab platform.
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The interaction of 2-(5-methyl-2-phenyl-2h-1,2,3-diazaphosphol-4-yl)-4h-benzo[e]-1,3,2-dioxaphosphinin-4-one with activated carbonyl compounds. Synthesis of bis-heterocyclic systems containing di- and tetracoordinated phosphorus
2017Co-Authors: Vladimir F. Mironov, Dmitry B. Krivolapov, Ekaterina V. Mironova, L M Abdrakhmanova, Gulnara A. Ivkova, Rashid Z. Musin, Aidar T. GubaidullinAbstract:The interaction of 2-(5-methyl-2-phenyl-2H-1,2,3-diazaphosphol-4-yl)-4H-benzo[e]-1,3,2-dioxaphosphinin-4-one with mesoxalic and trifluoropyruvic acids ethyl and diethyl esters, Hexafluoroacetone and chloral proceeds with an exclusive participation of P(III) atom and allows to obtain 2-(5-methyl-2-phenyl-2H-1,2,3-diazaphosphol-4-yl)-derivatives of 1,4,2- and 1,3,2-dioxaphosphepines as well as dichlorovinylphosphonate, being the product of Perkow reaction in the case of chloral.
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synthesis crystal structure and hydrolysis of novel isomeric cage p c p o phosphoranes on the basis of 4 4 5 5 tetramethyl 2 2 oxo 1 2 diphenylethoxy 1 3 2 dioxaphospholane and Hexafluoroacetone
RSC Advances, 2016Co-Authors: N R Khasiyatullina, Dmitry B. Krivolapov, V F Mironov, E V Mironova, O I GnezdilovAbstract:The reaction of 4,4,5,5-tetramethyl-2-(2-oxo-1,2-diphenylethoxy)-1,3,2-dioxaphospholane with Hexafluoroacetone leads to the simultaneous formation of regioisomeric cage (P–C/P–O)-phosphoranes, the structures of which are unequivocally confirmed by XRD. The rearrangement of the P–C-isomer to P–O-isomer with high stereoselectivity (>96%) takes place in methylene chloride solution with the retention of the phosphorus coordination. It was found that the stepwise hydrolysis of the P–O-isomer initially gives 2-(2,3-dihydroxy-1,2-diphenyl-3-trifluoromethyl-4,4,4-trifluorobutyloxy)-4,4,5,5-tetramethyl-2-oxo-1,3,2-dioxaphospholane as the only stereoisomer whose structure is also confirmed by XRD. Further hydrolysis of this compound leads to the formation of 2,3-dihydroxy-3-trifluoromethyl-4,4,4-trifluoro-1,2-diphenylbutylphosphate and pinacol, which forms the solvate in the crystal. Hydrolysis of the P–C-isomer yields 2-hydroxy-4,4,5,5-tetramethyl-2-oxo-1,3,2-dioxaphospholane, benzoin and hexafluoroisopropanol.
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stereoselective pco poc rearrangement of p c cage phosphorane in the reaction of 4 5 dimethyl 2 2 oxo 1 2 diphenyl ethoxy 1 3 2 dioxaphospholane with Hexafluoroacetone
Journal of Organic Chemistry, 2016Co-Authors: V F Mironov, Mudaris N. Dimukhametov, Sergey V. Efimov, Roza M. Aminova, Farida Kh. Karataeva, Dmitry B. Krivolapov, Ekaterina V. Mironova, Vladimir V. KlochkovAbstract:Interaction of 4,5-dimethyl-2-(2-oxo-1,2-diphenyl)ethoxy-1,3,2-dioxaphospholane, bearing a carboxyl group in the γ-position with respect to the phosphorus atom and obtained from d,l-butanediol, with Hexafluoroacetone (CCl4, −40 °C) leads to the simultaneous formation of regio- and stereoisomeric cage-like phosphoranes with phosphorus–carbon and phosphorus–oxygen bonds with a high stereoselectivity (>95%), whose structure was determined by 1D and 2D NMR spectroscopy and XRD. When stored as a solution in dichloromethane for one month, the PCO-isomer rearranges into the thermodynamically more stable POC-isomer of the cage-like phosphorane. Mild hydrolysis of the PCO/POC-isomers proceeds with a high chemoselectivity and leads to the formation of P(IV)-dioxaphospholane derivatives. Acidic hydrolysis of the POC-isomer leads to the formation of an oxirane derivative with an unexpectedly high stereoselectivity (>95%). DFT calculations (using the PBE functional) allowed us to obtain structures and energies of the ...
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Stereoselective PCO/POC-Rearrangement of P–C-Cage Phosphorane in the Reaction of 4,5-Dimethyl-2-(2-oxo-1,2-diphenyl)ethoxy-1,3,2-dioxaphospholane with Hexafluoroacetone
2016Co-Authors: Vladimir F. Mironov, Mudaris N. Dimukhametov, Sergey V. Efimov, Roza M. Aminova, Farida Kh. Karataeva, Dmitry B. Krivolapov, Ekaterina V. Mironova, Vladimir V. KlochkovAbstract:Interaction of 4,5-dimethyl-2-(2-oxo-1,2-diphenyl)ethoxy-1,3,2-dioxaphospholane, bearing a carboxyl group in the γ-position with respect to the phosphorus atom and obtained from d,l-butanediol, with Hexafluoroacetone (CCl4, −40 °C) leads to the simultaneous formation of regio- and stereoisomeric cage-like phosphoranes with phosphorus–carbon and phosphorus–oxygen bonds with a high stereoselectivity (>95%), whose structure was determined by 1D and 2D NMR spectroscopy and XRD. When stored as a solution in dichloromethane for one month, the PCO-isomer rearranges into the thermodynamically more stable POC-isomer of the cage-like phosphorane. Mild hydrolysis of the PCO/POC-isomers proceeds with a high chemoselectivity and leads to the formation of P(IV)-dioxaphospholane derivatives. Acidic hydrolysis of the POC-isomer leads to the formation of an oxirane derivative with an unexpectedly high stereoselectivity (>95%). DFT calculations (using the PBE functional) allowed us to obtain structures and energies of the initial phospholane, reaction products (PCO/POC-isomers), and an intermediate P(V)-oxaphosphirane
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reactions of 2 5 methyl 2 phenyl 2h 1 2 3 diazaphosphol 4 yl 4h 1 3 2 benzodioxaphosphinin 4 one with chloral and Hexafluoroacetone
Mendeleev Communications, 2011Co-Authors: Dmitry B. Krivolapov, V F Mironov, L M Abdrakhmanova, G A Ivkova, E V Mironova, I V KonovalovaAbstract:Abstract Reaction of 2-(5-methyl-2-phenyl-2H-1,2,3-diazaphosphol-4-yl)-4H-1,3,2-benzodioxaphosphinin-4-one with chloral occurs at Piii atom of the 1,3,2-dioxaphosphinine cycle giving mostly 2-chlorocarbonylphenyl 2,2-dichlorovinyl (5-methyl-2-phenyl-2H-1,2,3-diazaphosphol-4-yl)phosphonate, whereas Hexafluoroacetone incorporates into the 1,3,2-dioxaphosphorine cycle affording the corresponding 1,3,2-benzodioxaphosphepine.
E V Mironova - One of the best experts on this subject based on the ideXlab platform.
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tandem dihetero diels alder and huisgen cycloaddition reactions synthesis crystal structure and hydrolysis of the novel cage phosphoranes
Organic chemistry frontiers, 2018Co-Authors: I A Litvinov, R Z Musin, S V Efimov, E V Mironova, T A Baronova, N R Khasiyatullina, Robert R Fayzullin, V V KlochkovAbstract:The reaction of 2-(1-phenylvinyloxy)benzo-1,3,2-dioxaphosphole with Hexafluoroacetone, ethyltrifluoropyruvate and chloral leads to the formation of cage phosphoranes possessing the 1-phospha-2,6,8-trioxabicyclo[3.2.1]octane framework whose structure was established by the XRD method and NMR spectroscopy. The process involves dihetero-Diels–Alder and Huisgen 1,3-dipolar cycloaddition reactions and is accompanied by the simultaneous formation of the P–C and C–C bonds. Despite the generation of three chiral carbon atoms, the stereoselectivity of the process exceeds 96%. Hydrolysis leads to the formation of functionalized aldols and phosphonates.
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synthesis crystal structure and hydrolysis of novel isomeric cage p c p o phosphoranes on the basis of 4 4 5 5 tetramethyl 2 2 oxo 1 2 diphenylethoxy 1 3 2 dioxaphospholane and Hexafluoroacetone
RSC Advances, 2016Co-Authors: N R Khasiyatullina, Dmitry B. Krivolapov, V F Mironov, E V Mironova, O I GnezdilovAbstract:The reaction of 4,4,5,5-tetramethyl-2-(2-oxo-1,2-diphenylethoxy)-1,3,2-dioxaphospholane with Hexafluoroacetone leads to the simultaneous formation of regioisomeric cage (P–C/P–O)-phosphoranes, the structures of which are unequivocally confirmed by XRD. The rearrangement of the P–C-isomer to P–O-isomer with high stereoselectivity (>96%) takes place in methylene chloride solution with the retention of the phosphorus coordination. It was found that the stepwise hydrolysis of the P–O-isomer initially gives 2-(2,3-dihydroxy-1,2-diphenyl-3-trifluoromethyl-4,4,4-trifluorobutyloxy)-4,4,5,5-tetramethyl-2-oxo-1,3,2-dioxaphospholane as the only stereoisomer whose structure is also confirmed by XRD. Further hydrolysis of this compound leads to the formation of 2,3-dihydroxy-3-trifluoromethyl-4,4,4-trifluoro-1,2-diphenylbutylphosphate and pinacol, which forms the solvate in the crystal. Hydrolysis of the P–C-isomer yields 2-hydroxy-4,4,5,5-tetramethyl-2-oxo-1,3,2-dioxaphospholane, benzoin and hexafluoroisopropanol.
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reactions of 2 5 methyl 2 phenyl 2h 1 2 3 diazaphosphol 4 yl 4h 1 3 2 benzodioxaphosphinin 4 one with chloral and Hexafluoroacetone
Mendeleev Communications, 2011Co-Authors: Dmitry B. Krivolapov, V F Mironov, L M Abdrakhmanova, G A Ivkova, E V Mironova, I V KonovalovaAbstract:Abstract Reaction of 2-(5-methyl-2-phenyl-2H-1,2,3-diazaphosphol-4-yl)-4H-1,3,2-benzodioxaphosphinin-4-one with chloral occurs at Piii atom of the 1,3,2-dioxaphosphinine cycle giving mostly 2-chlorocarbonylphenyl 2,2-dichlorovinyl (5-methyl-2-phenyl-2H-1,2,3-diazaphosphol-4-yl)phosphonate, whereas Hexafluoroacetone incorporates into the 1,3,2-dioxaphosphorine cycle affording the corresponding 1,3,2-benzodioxaphosphepine.
Vladimir V. Klochkov - One of the best experts on this subject based on the ideXlab platform.
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stereoselective pco poc rearrangement of p c cage phosphorane in the reaction of 4 5 dimethyl 2 2 oxo 1 2 diphenyl ethoxy 1 3 2 dioxaphospholane with Hexafluoroacetone
Journal of Organic Chemistry, 2016Co-Authors: V F Mironov, Mudaris N. Dimukhametov, Sergey V. Efimov, Roza M. Aminova, Farida Kh. Karataeva, Dmitry B. Krivolapov, Ekaterina V. Mironova, Vladimir V. KlochkovAbstract:Interaction of 4,5-dimethyl-2-(2-oxo-1,2-diphenyl)ethoxy-1,3,2-dioxaphospholane, bearing a carboxyl group in the γ-position with respect to the phosphorus atom and obtained from d,l-butanediol, with Hexafluoroacetone (CCl4, −40 °C) leads to the simultaneous formation of regio- and stereoisomeric cage-like phosphoranes with phosphorus–carbon and phosphorus–oxygen bonds with a high stereoselectivity (>95%), whose structure was determined by 1D and 2D NMR spectroscopy and XRD. When stored as a solution in dichloromethane for one month, the PCO-isomer rearranges into the thermodynamically more stable POC-isomer of the cage-like phosphorane. Mild hydrolysis of the PCO/POC-isomers proceeds with a high chemoselectivity and leads to the formation of P(IV)-dioxaphospholane derivatives. Acidic hydrolysis of the POC-isomer leads to the formation of an oxirane derivative with an unexpectedly high stereoselectivity (>95%). DFT calculations (using the PBE functional) allowed us to obtain structures and energies of the ...
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Stereoselective PCO/POC-Rearrangement of P–C-Cage Phosphorane in the Reaction of 4,5-Dimethyl-2-(2-oxo-1,2-diphenyl)ethoxy-1,3,2-dioxaphospholane with Hexafluoroacetone
2016Co-Authors: Vladimir F. Mironov, Mudaris N. Dimukhametov, Sergey V. Efimov, Roza M. Aminova, Farida Kh. Karataeva, Dmitry B. Krivolapov, Ekaterina V. Mironova, Vladimir V. KlochkovAbstract:Interaction of 4,5-dimethyl-2-(2-oxo-1,2-diphenyl)ethoxy-1,3,2-dioxaphospholane, bearing a carboxyl group in the γ-position with respect to the phosphorus atom and obtained from d,l-butanediol, with Hexafluoroacetone (CCl4, −40 °C) leads to the simultaneous formation of regio- and stereoisomeric cage-like phosphoranes with phosphorus–carbon and phosphorus–oxygen bonds with a high stereoselectivity (>95%), whose structure was determined by 1D and 2D NMR spectroscopy and XRD. When stored as a solution in dichloromethane for one month, the PCO-isomer rearranges into the thermodynamically more stable POC-isomer of the cage-like phosphorane. Mild hydrolysis of the PCO/POC-isomers proceeds with a high chemoselectivity and leads to the formation of P(IV)-dioxaphospholane derivatives. Acidic hydrolysis of the POC-isomer leads to the formation of an oxirane derivative with an unexpectedly high stereoselectivity (>95%). DFT calculations (using the PBE functional) allowed us to obtain structures and energies of the initial phospholane, reaction products (PCO/POC-isomers), and an intermediate P(V)-oxaphosphirane
N R Khasiyatullina - One of the best experts on this subject based on the ideXlab platform.
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tandem dihetero diels alder and huisgen cycloaddition reactions synthesis crystal structure and hydrolysis of the novel cage phosphoranes
Organic chemistry frontiers, 2018Co-Authors: I A Litvinov, R Z Musin, S V Efimov, E V Mironova, T A Baronova, N R Khasiyatullina, Robert R Fayzullin, V V KlochkovAbstract:The reaction of 2-(1-phenylvinyloxy)benzo-1,3,2-dioxaphosphole with Hexafluoroacetone, ethyltrifluoropyruvate and chloral leads to the formation of cage phosphoranes possessing the 1-phospha-2,6,8-trioxabicyclo[3.2.1]octane framework whose structure was established by the XRD method and NMR spectroscopy. The process involves dihetero-Diels–Alder and Huisgen 1,3-dipolar cycloaddition reactions and is accompanied by the simultaneous formation of the P–C and C–C bonds. Despite the generation of three chiral carbon atoms, the stereoselectivity of the process exceeds 96%. Hydrolysis leads to the formation of functionalized aldols and phosphonates.
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synthesis crystal structure and hydrolysis of novel isomeric cage p c p o phosphoranes on the basis of 4 4 5 5 tetramethyl 2 2 oxo 1 2 diphenylethoxy 1 3 2 dioxaphospholane and Hexafluoroacetone
RSC Advances, 2016Co-Authors: N R Khasiyatullina, Dmitry B. Krivolapov, V F Mironov, E V Mironova, O I GnezdilovAbstract:The reaction of 4,4,5,5-tetramethyl-2-(2-oxo-1,2-diphenylethoxy)-1,3,2-dioxaphospholane with Hexafluoroacetone leads to the simultaneous formation of regioisomeric cage (P–C/P–O)-phosphoranes, the structures of which are unequivocally confirmed by XRD. The rearrangement of the P–C-isomer to P–O-isomer with high stereoselectivity (>96%) takes place in methylene chloride solution with the retention of the phosphorus coordination. It was found that the stepwise hydrolysis of the P–O-isomer initially gives 2-(2,3-dihydroxy-1,2-diphenyl-3-trifluoromethyl-4,4,4-trifluorobutyloxy)-4,4,5,5-tetramethyl-2-oxo-1,3,2-dioxaphospholane as the only stereoisomer whose structure is also confirmed by XRD. Further hydrolysis of this compound leads to the formation of 2,3-dihydroxy-3-trifluoromethyl-4,4,4-trifluoro-1,2-diphenylbutylphosphate and pinacol, which forms the solvate in the crystal. Hydrolysis of the P–C-isomer yields 2-hydroxy-4,4,5,5-tetramethyl-2-oxo-1,3,2-dioxaphospholane, benzoin and hexafluoroisopropanol.