Cyclophosphorylation of polyphenols by diamidoarylphosphites

Maslennikova, V. I.; Merkulov, Roman V.; Dyagileva, Maria V.; Vasyanina, L. K.; Antipin, M. Yu.; Weber, Dirk; Бауер, И.; Habicher, Wolf D.; Nifantyev, E. E.

doi:10.1016/s0040-4020(03)00111-x

Cited by 7 publications

(12 citation statements)

References 8 publications

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“…2a,b). A narrow singlet in the 31 P NMR spectrum and a set of signals for the protons of the resorcinarene matrix in the 1 H NMR spectrum are typical for rigid phosphocyclic calixarene structures 18,19 . The averaging of signals for the protons of the macrocyclic skeleton in phosphocavitands is due to the symmetry of their molecules.…”

Section: Methodsmentioning

confidence: 99%

New aspects in the chemistry of perphosphorylated calix[4]resorcinarenes

Nifantyev¹,

Maslennikova²,

Habicher³

et al. 2004

Arkivoc

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Interaction between calix[4]resorcinarenes 1 and 2-amino-1,3,2-diheterophosphorinanes 2 resulted in sterically pure polyphosphocyclic conjugates 3. The structure of which was supported by NMR spectroscopy and X-ray diffraction analysis. The possibility of further modification of perphosphorylated resorcinarenes 3 was studied. It was shown that compounds 3a,b containing tBu-N groups at the phosphorus atoms do not enter into reactions increasing the coordination number of phosphorus because of steric hindrance. Sterically less hindered phosphoresorcinarenes 3c-i readily add sulfur, oxygen, and form octanuclear and chelate complexes with transition metals (Mo and Pd, respectively).

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Section: Methodsmentioning

confidence: 99%

New aspects in the chemistry of perphosphorylated calix[4]resorcinarenes

Nifantyev¹,

Maslennikova²,

Habicher³

et al. 2004

Arkivoc

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“…140,149,150 Apparently, the reaction proceeds in two steps. The first step occurs via the classical mechanism of phosphorylation of alcohols and phenols accompanied by the cleavage of one P7N bond to form the corresponding intermediate 191.…”

Section: Design Of Phosphocavitandsmentioning

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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“…Cyclophosphorylation of Resorcinarenes with Phosphorus Amides. We have proposed and studied in detail the amide method of phosphorylation of resorcinarenes, 7,[16][17][18][19][20][21][22] which made accessible many types of stereochemically pure phosphocavitands. Note that this method has later been used by other research groups, for example, see refs 23-26. Phosphorus triamides and alkyl and aryl phosphorodiamidites have been used as cyclophosphorylation reagents (Scheme 4).…”

Section: Synthesis Of Phosphocavitandsmentioning

confidence: 99%

“…18 Meanwhile, cyclophosphorylation of resorcinarenes with isopropyl and benzyl phosphorodiamidites gave mainly symmetrical stereoisomers. [18][19][20] Thus, in these cases, the process can be classified as stereoselective.…”

Section: Synthesis Of Phosphocavitandsmentioning

confidence: 99%

“…The cyclophosphorylation of resorcinarenes 1 with aliphatic ester amides followed, in all cases, the classical pattern with cleavage of two P-N bonds and formation of phosphitocavitands [17][18][19]21 (Scheme 4). However, the use of phosphorus ester diamides with aromatic groups brings about an abnormal reaction route, 20,22 which is of fundamental importance. Conventionally, this process can be divided into two steps (Scheme 5).…”

Section: Intramolecular Control Of the Regioselectivity Of The Cyclop...mentioning

confidence: 99%

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Design and Study of PhosphocavitandsA New Family of Cavity Systems

2004

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The design of phosphorus-containing cavity architectures that are of interest for biomimetics and other interdisciplinary sciences is among the most high-priority lines of research in modern organophosphorus chemistry. This Account acquaints the readers with methods for the design of rigid phosphomacrocyclic systems based on resorcinarenes, which differ in the nature of the phosphorus functions on the upper rim of the molecular bowl and have fixed dimensions of the molecular cavity. The authors demonstrate the possibility of attaining stereoselectivity in the synthesis of phospho(III)cavitands and their various transformations.

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Cyclophosphorylation of polyphenols by diamidoarylphosphites

Cited by 7 publications

References 8 publications

New aspects in the chemistry of perphosphorylated calix[4]resorcinarenes

New aspects in the chemistry of perphosphorylated calix[4]resorcinarenes

Phosphorus-containing macrocyclic compounds: synthesis and properties

Design and Study of PhosphocavitandsA New Family of Cavity Systems

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