The reaction of 2-ethoxy-3-phenylbenzo[ d ]-1,3, 2-oxazaphosphorin-6-one with α-ketocarboxylic acid esters: Synthesis of benzo[ d ]-1,3,2-oxazaphosphepine derivatives

The reactions of 2-ethoxy-3-phenylbenzo[d]-1,3,2-oxazaphosphorin-6-one with R-carbonylcarboxylic acids ethyl esters (R = CF3, Ph, and Me) lead to the formation of seven-membered heterocycles, 2-ethoxy-9-ethoxycarbonyl-2,8- dioxo-3-phenyl-9-R-benzo[d]-1,3,2-oxazaphosphepines. © 2013 Copyright Taylor and Francis Group, LLC

Tetracoordinate phosphorus cage compounds with endocyclic P–C bonds: Synthesis and reactivity

© 2016, Pleiades Publishing, Ltd.The survey summarizes modern methods of synthesis and reactivity of tetracoordinated phosphorus cage compounds containing one or more endocyclic P–C bonds (phosphine oxides, phosphinates and phosphonates, phosphatripticenes and others). Intramolecular cyclization reactions including electrophilic aromatic substitution with unsaturated organophosphorus compounds, reactions of P–H-derivatives with carbonyl compounds as well as cycloaddition reactions involving I–IV-coordinated phosphorus derivatives are considered

Synthesis and some properties of 2-(5-methyl-2-phenyl-2 h -1,2,3-diazaphosphol-4-yl)-4 h -benzo[ d ]-1,3,2-dioxaphosphorin-4-one

2-(5-Methyl-2-phenyl-2-1,2,3-diazaphosphol-4-yl)-4H-benzo[d]-1,3, 2-dioxaphosphorin-4-one 1 readily reacts with hexafluoroacetone, mesoxalic acid diethyl ester, trifluoropyruvic acid ethyl ester and chloral to give 2-(5-methyl-2-phenyl-2H-1,2,3-dizaphosphole-4-yl)-derivatives of 1,3,2- and 1,4,2-dioxaphosphepines. © 2013 Copyright Taylor and Francis Group, LLC

Functionalized phosphoryl compounds: Synthesis, extraction, transport and ionophore properties

The row of phosphoryl compounds, having additional functional groups with complexating abilities were synthesized via the classical methods of the organophosphorus chemistry. The extraction properties of the mono- and biphosphorilated amines were investigated and it is shown the high efficiency and selectivity of the noble metal ions extraction from acid water solutions. Some phosphorylated azapodands were obtained by Kabachnik-Fields reaction and their membrane transport and ionophoric properties were investigated. Copyright © Taylor & Francis Group, LLC

Cycloexpansion reactions in benzo[e]-1,3,2-diheterophosphorin-4-ones and 4-oxo-1,3,2-dioxaphospholanes

The peculiarities of the reactions of 2-R-benzo[d]-1,3,2-dioxaphosphorin-4- ones, 2-R-naphtho[d]-1,3,2-dioxaphosphorin-4-ones, 2-R-8-azabenzo[e]-1,3,2- dioxaphosphorin-4- ones, and 2-R-1,3,2-dioxaphospholan-4-ones with unsaturated compounds are summarized in the review. The reactions proceed in the mild conditions and lead to the formation of the seven- and six-membered heterocycles 1,3,2-dioxa-, 1,3,2-oxaza-, 1,4,2-dioxa-, and 1,4,2- oxazaphosphepines and 1,3,2- and 1,4,2-dioxaphosphorinanes with a high regio- and stereoselectivity. The hydrolysis and thermolysis of the some benzophosphepine derivatives leads to the substituted fluorinated ketones and various nonphosphorus heterocycles. Copyright © Taylor & Francis Group, LLC

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

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. © 2011 Mendeleev Communications. All rights reserved

Features of Reaction of 2-(5-Methyl-2-phenyl-2H-1,2,3-diazaphosphol-4-yl)-4H-benzo[e]-1,3,2-dioxaphosphorin-4-one with 1,2-Dicarbonyl Compounds

© 2018, Pleiades Publishing, Ltd. 2-(5-Methyl-2-phenyl-2H-1,2,3-diazaphosphol-4-yl)-4H-benzo[e]-1,3,2-dioxaphosphorin-4-one reacts with perfluorodiacetyl, 3,6-di(tert-butyl)-1,2-benzoquinone and phenanthrenequinone only with the participation of a three-coordinated phosphorus atom to form spirophosphoranes containing acyclic 5-methyl-2- phenyl-2H-1,2,3-diazaphosphol-4-yl substituent, whereas the interaction with tetrachloro-1,2-benzoquinone proceeds via expanding the six-membered heterocycle to the nine-membered one to form 2-(2-phenyl-2H-1,2,3-diazaphosphol-4-yl)-2,9-dioxo-4,5,6,7-tetrachlorodibenzo[d,h]-1,3,8-trioxaphosphonine

Caged phosphorane with P-C bond based on chloral and 4,5-dimethyl-2-(2-oxo-1,2-diphenylethoxy)-1,3,2-dioxaphospholane

© 2015 Pleiades Publishing, Ltd. The key methods of caged phosphoranes synthesis are analyzed. Reaction of 4,5-dimethyl-2-(2-oxo-1,2-diphenylethoxy)-1,3,2-dioxaphospholane (prepared from the meso-form of 2,3-butanediol) with chloral has yielded the caged phosphorane containing a phosphorus-carbon bond: 1,1-(1,2-dimethylethylenedioxy)-3,4-diphenyl-6-trichloromethyl-2,5,7,1-trioxaphosphabicyclo[2.2.11,4]heptane; spatial structure of the product has been elucidated with X-ray diffraction analysis

Specific features of reaction of 2-R-benzo[e][1,3,2]dioxaphosphinin-4-ones with perfluorodiacetyl. Synthesis and steric structure of 4′,5′- bis(trifluoromethyl)-4-oxo-2-(2,2,3,3-tetrafluoropropoxy)-2λ 5-spiro[benzo[e][1,3,2]dioxaphosphinine-2,2′-[1,3,2] dioxaphosphole]

2-R-benzo[e][1,3,2]dioxaphosphinin-4-ones react with perfluorodiacetyl under mild conditions to form relatively labile spirophosphoranes containing a 1,3,2-dioxaphosphole ring. These compounds gradually convert to more stable 2-R-4,5-bis(trifluoromethyl)-1,3,2λ5-dioxaphosphole 2-oxides and diastereometic 2-R-4-(trifluoroacetyl)-4-(trifluoromethyl)benzo[f][1,3, 2λ5]dioxaphosphepine 2-oxides, whose structure was confirmed by means of NMR and IR spectroscopy. The structure of 4′,5′ -bis(trifluoromethyl)-4-oxo-2-(2,2,3,3-tetrafluoropropoxy)-2λ 5-spiro[benzo[e][1,3,2]dioxaphosphinine-2,2′-[1,3,2] dioxaphosphole] was confirmed by X-ray diffraction analysis. ©2005 Pleiades Publishing, Inc

Reactions of 2-phenyl-4,4-bis(trifluoromethyl)-4,5-dihydro-1,3,2- benzodioxaphosphepin-5-one with phenanthrenequinone and dibenzoyl

Reactions of 2-phenyl-4,4-bis(trifluoromethyl)-4,5-dihydro-1,3,2- benzodioxaphosphepin-5-one with 9,10-phenanthrenequinone and dibenzoyl gave hydrolytically unstable spirophosphoranes with five- and seven-membered rings, 2-phenyl-4,4-bis(trifluoromethyl)-4,5-dihydrospiro[[1,3,2]benzodioxaphosphepine- 2,2′-phenanthro[9,10-d][1,3,2]dioxaphosphol]-5-one and 2,4′,5′-triphenyl-4,4-bis(trifluoromethyl)-4,5-dihydrospiro[[ 1,3,2]benzodioxaphosphepine-2,2′-[1,3,2]dioxaphosphol]-5-one. The structure of the first of these was proved by X-ray analysis. © Pleiades Publishing, Ltd., 2011