Novel P,N-Containing Cyclophane with a Chiral Hydrophobic Cavity

Карасик, А. А.; Kulikov, Dmitrii V.; Kuznetsov, Roman M.; Balueva, A. S.; Akhmetgaliev, Artur A.; Kataeva, О. N.; Lönnecke, Peter; Sharapov, Oleg R.; Zhelezina, Yulia A.; Ignat’eva, S. N.; Hey‐Hawkins, Evamarie; Sinyashin, Оleg G.

doi:10.6060/mhc2011.4.08

Cited by 12 publications

(4 citation statements)

References 14 publications

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“…46 These investigations were successfully continued using N-alkyl-2,6-diamino-9,10-dihydro-9,10-ethanoanthracenes as reactants in the condensation with bis(hydroxyethyl)phenylphosphine. 46,181 3. One-step formation of the phosphorus-containing calix [4]…”

Section: Synthesis Of Macrocyclic Polyphosphines and Their Derivativesmentioning

confidence: 99%

Phosphorus-containing macrocyclic compounds: synthesis and properties

Knyazeva¹,

Бурилов²,

Пудовик³

et al. 2013

Russ. Chem. Rev.

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Main trends in the development of methods for Main trends in the development of methods for the synthesis of phosphorus-containing macrocyclic com-the synthesis of phosphorus-containing macrocyclic compounds in the past 15 years are considered. Emphasis is pounds in the past 15 years are considered. Emphasis is given to reactions producing macrocyclic structures with the given to reactions producing macrocyclic structures with the participation of a phosphorus atom and other functional participation of a phosphorus atom and other functional groups involved in organophosphorus molecules and to groups involved in organophosphorus molecules and to modifications of macrocycles by phosphorus compounds modifications of macrocycles by phosphorus compounds in different valence states. Possibilities of the practical in different valence states. Possibilities of the practical application of phosphorus-containing macrocyclic com-application of phosphorus-containing macrocyclic compounds in difference areas of science and engineering are pounds in difference areas of science and engineering are discussed. The bibliography includes 205 references discussed. The bibliography includes 205 references. .

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Section: Synthesis Of Macrocyclic Polyphosphines and Their Derivativesmentioning

confidence: 99%

Phosphorus-containing macrocyclic compounds: synthesis and properties

Knyazeva¹,

Бурилов²,

Пудовик³

et al. 2013

Russ. Chem. Rev.

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“…Various 28-, 36-, 38- and 46-membered P,N-containing cyclophanes with 1,5-diaza-3,7-diphosphacyclooctane fragments incorporated into the macrocyclic backbone have been obtained by stereoselective covalent self-assembly between primary phosphines, formaldehyde, and diamines with spatially divided amino groups [ 19 , 20 , 21 , 22 , 23 , 24 , 25 ]. Later, their coordination properties towards metals of groups VI, VIII, and X have been studied [ 26 , 27 , 28 , 29 ].…”

Section: Introductionmentioning

confidence: 99%

“…Later, their coordination properties towards metals of groups VI, VIII, and X have been studied [ 26 , 27 , 28 , 29 ]. In the uncoordinated cyclophanes, the eight-membered 1,5-diaza-3,7-diphosphacyclooctane fragments adopt a “crown” conformation in which the phosphorus electron lone pairs are directed inside the macrocycle cavity [ 20 , 22 , 23 , 24 , 25 ]. It has been shown that complex formation with groups VI and VIII metals of these macrocycles led to dramatic changes in the initial conformations of the ligands; thus, the metal-containing moieties of the forming binuclear bis-P,P-chelate complexes were located outside the macrocyclic cavities [ 26 , 27 , 28 , 29 ].…”

Section: Introductionmentioning

confidence: 99%

First Example of Cage P4N4-Macrocycle Copper Complexes with Intracavity Location of Unusual Cu2I Fragments

et al. 2023

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In this study, 28-membered macrocyclic 1,5(1,5)-di(1,5-diaza-3,7-diphosphacyclooctana)-2,4,6,8(1,4)-tetrabenzenacyclooctaphane were synthesized by condensation of pyridinephosphine, paraformaldehyde, and primary diamines (bis(4-aminophenyl)methane or –sulfide. The first representatives of binuclear copper(I) complexes of P,N-containing cyclophanes with two 1,5-diaza-3,7-diphosphacyclooctane rings incorporated into a macrocyclic core and intracavity location of unusual, developed angle Сu2I moiety were obtained. The structure of one complex was established by X-ray diffraction analysis. The complexation led to a slight distortion of the cyclophane conformations.

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“…The successful use of this strategy has resulted in the synthesis of a series of 28-38-membered cage macrocyclic tetraphoshines with two diazadiphosphacyclooctane rings and various phane fragments depending on the nature of starting diamines. [18,21,22] The use of available pyridyl-containing primary phosphines, namely (pyridine-2-yl)phosphine [10,23] and [2-(pyridine-2-yl)ethylphosphine [24] in analogous condensations could become a route to the synthesis of functionalized P,N-containing cyclophanes with pyridyl-containing groups on the periphery. In the present paper we describe the synthesis of the first representatives of 28-and 36-membered cage P,N-containing macrocycles with pyridyl-and pyridylethyl substituents on phosphorus atoms on the basis of the covalent selfassembly approach.…”

Section: Introductionmentioning

confidence: 99%

New P,N-Containing Cyclophanes with Exocyclic Pyridyl Containing Substituents on Phosphorus Atoms

Nikolaeva¹,

Balueva²,

Musina³

et al. 2015

MHC

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The synthesis of 28-and 36-membered P,N-containing cyclophanes with two 1,5-diaza-3,7-diphosphacyclooctane (17-21 %) whereas the condensations with the participation of 1,3-bis(4'-aminophenoxy) benzene containing three phenylene groups in the spacer are much less selective, and 36-membered cyclophanes have been obtained in low yields (7-9 %). It shows the strong influence of the starting phosphine nature on the selectivity of the Mannich-like condensation reactions. The treatment of 28-membered P-pyridylethyl substituted cyclophanes with hydrochloric acid in chloroform leads to the corresponding monohydrochlorides as a result of the protonation of pyridyl nitrogen atom, and in the solutions the fast migration of the proton between all pyridyl nitrogen centers is observed.Keywords: Macrocycle, cyclophane, pyridyl-containing phosphine, diamine, condensation, covalent self-assembly.Новые P,N -содержащие циклофаны с экзоциклическими пиридилсодержащими заместителями при атомах фосфора

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Novel P,N-Containing Cyclophane with a Chiral Hydrophobic Cavity

Abstract: The effective self-assembly process between phenylphosphine, formaldehyde and racemic N-alkyl-2,6-diamino-9,10-dihydro-9,10-ethanoanthracene-11,12-dicarboximides

Cited by 12 publications

References 14 publications

Phosphorus-containing macrocyclic compounds: synthesis and properties

Phosphorus-containing macrocyclic compounds: synthesis and properties

First Example of Cage P4N4-Macrocycle Copper Complexes with Intracavity Location of Unusual Cu2I Fragments

New P,N-Containing Cyclophanes with Exocyclic Pyridyl Containing Substituents on Phosphorus Atoms

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