Design and study of phosphocavitands - A new family of cavity systems

Accounts of Chemical Research

Volumn 38, Issue 2, 2005, Pages 108-116

  Nifantyev, Eduard E ^a,b,c,d,e,f   Maslennikova, Vera I ^a   Merkulov, Roman V ^a,b,d,g  

^a MOSCOW STATE PEDAGOGICAL UNIVERSITY   (Russian Federation)

^b A N NESMEYANOV INSTITUTE OF ORGANOELEMENT COMPOUNDS   (Russian Federation)

^c RUSSIAN ACADEMY OF SCIENCES   (Russian Federation)

^d M V Lomonosov Moscow State Univ ^*

^e MOSCOW STATE UNIVERSITY   (Russian Federation)

^f Russian Academy of Sciences   (Russian Federation)

^g Moscow Pedagogical State University

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; CHLORIDE; FUNCTIONAL GROUP; MACROCYCLIC COMPOUND; ORGANOPHOSPHORUS COMPOUND; PHOSPHORUS; PHOSPHORUS ACID DERIVATIVE; PHOSPHORUS DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE;

ADDITION REACTION; ARTICLE; CHEMICAL MODIFICATION; COMPLEX FORMATION; COMPUTER SIMULATION; NUCLEAR MAGNETIC RESONANCE; OXIDATION; PHOSPHORYLATION; REACTION ANALYSIS; STEREOCHEMISTRY; STEREOISOMERISM; STRUCTURE ANALYSIS; X RAY DIFFRACTION;

CYCLIZATION; ETHERS, CYCLIC; MOLECULAR STRUCTURE; ORGANOPHOSPHORUS COMPOUNDS; PHENYLALANINE; PHOSPHORYLATION; RESORCINOLS;

EID: 13944262617     PISSN: 00014842     EISSN: None     Source Type: Journal    
DOI: 10.1021/ar0401810     Document Type: Article

References (47)

1. Pedersen, C. J. The discovery of crown ethers (Nobel Lecture). Angew. Chem., Int. Ed. Engl. 1988, 27, 1021-1027.
2. Lehn, J.-M. Supramolecular chemistry - scope and perspectives: molecules, supermolecules, and molecular devices (Nobel Lecture). Angew. Chem., Int. Ed. Engl. 1988, 27, 89-112.
3. Cram, D. J. The design of molecular hosts, guests, and their complexes (Nobel Lecture) Angew. Chem., Int. Ed. Engl. 1988, 27, 1009-1020.
4. Moran, J. R.; Karbach, S.; Cram, D. J. Cavitands: synthetic molecular vessels. J. Am. Chem. Soc. 1982, 104, 5826-5828.
5. Cram, D. J. Molecular container compounds. Nature 1992, 356, 29-36.
6. 4-halide binding. J. Am. Chem. Soc. 1993, 115, 6456-6457.
7. Nifantyev, E. E.; Maslennikova, V. I.; Vasyanina, L. K.; Panina, E. V. On the potential of phosphorylation and cyclophosphorylation of procavitands with phosphorous amides. Zh. Obshch. Khim. 1994, 64, 154-155.
8. Lippmann, T.; Wilde, H.; Dalcanale, E.; Mann, G. Synthesis and configuration analysis of phosphorus bridged cavitands. Tetrahedron Lett. 1994, 35, 1685-1688.
9. Vollbrecht, A.; Neda, I.; Thonnessen, H.; Jones, P. G.; Harris, R. K.; Crowe, L. A.; Schmutzler; R. Synthesis, structure, and reactivity of tetrakis(O, O-phosphorus)-bridged calix[4]resorcinols and their derivatives. Chem. Ber. 1997, 130, 1715-1720.
10. Lippmann, T.; Wilde, H.; Dalcanale, E.; Mavilla, L.; Mann, G.; Heyer, V.; Spera, S. Synthesis and Configurational Analysis of a Novel Class of Cavitands Containing Four Dioxaphosphocin Moieties. J. Org. Chem. 1995, 60, 235-242.
11. Dalcanale, E.; Jacopozzi, P.; Ugozzoli, F.; Mann, G. Synthesis and Configurational analysis of mixed-bridged phosphate cavitands. Supramol. Chem. 1998, 9 (4), 305-316.
12. Jacopozzi, P.; Dalcanale, E.; Spera, S.; Chrisstoffels, L. A. J.; Reinhoudt, D. N.; Lippmann, T.; Mann, G. Synthesis and Configurational analysis of phosphonate cavitands. J. Chem. Soc., Perkin. Trans. 2. 1998, 3, 671-678.
13. Nuutinen, J. M. J.; Irico, A.; Vincenti, M.; Dalcanale, E.; Pakarinen, J. M. H.; Vainiotalo, P. Gas-phase ion-molecule reactions between a series of protonated diastereomeric cavitands and neutral amines studied by ESI-FTICRMS: gas-phase inclusion complex formation. J. Am. Chem. Soc. 2000, 122, 10090-10100.
14. Delangle, P.; Mulatier, J. C.; Tinant, B.; Declercq, J. P.; Dutasta, J. P. Synthesis and Binding Properties of iiii (4i) Stereoisomers of Phosphonato Cavitands - Cooperative Effects in Cation Complexation in Organic Solvents. Eur. J. Org. Chem. 2001, 19, 3695-3704.
15. Bibal, B.; Tinant, B.; Declercq, J. P.; Dutasta, J. P. Preparation and structure of [iiii]tetraphosphonatocavitands bearing long chain functionlity at the lower rim: metal picrates extraction studies. Supramol. Chem. 2003, 15 (1), 25-32.
16. Nifantyev, E. E.; Maslennikova, V. I.; Panina, E. V.; Bekker, A. R.; Vasyanina, L. K.; Lysenko, R. A.; Antipin, M. Yu.; Struchkov, Yu. T. Synthesis and Structure of Phosphito- and Thiophosphatocavitands. Mendeleev Commun. 1995, 131-133.
17. Maslennikova, V. I.; Shkarina, E. V.; Bekker A. R.; Vasyanina, L. K.; Nifantyev, E. E. Amidophosphites in the chemistry of calix[4]-resorcinolarene. Phosphorus, Sulfur Silicon 1996, 113, 219-223.
18. Maslennikova, V. I.; Shkarina, E. V.; Vasyanina, L. K.; Lysenko, K. A.; Antipin, M. Yu.; Nifantyev, E. E. Phosphacavitands: I. Phosphorylation of Calix[4]resorcinolarenes with Phosphorous Amides. Synthesis of First Cavitands Derived from Phosphoramidites. Russ. J. Gen. Chem. 1998, 68, 350-361.
19. Maslennikova, V. I.; Shkarina, E. V.; Vasyanina, L. K.; Lysenko, K. A.; Sinicina, T. K.; Merkulov, R. V.; Nifantyev, E. E. Tetrapropylphosphocavitands: synthesis, structure, and properties. Phosphorus, Sulfur Silicon 1998, 139, 173-186.
20. Maslennikova, V. I.; Merkulov, R. V.; Dyagileva, M. V.; Vasyanina, L. K.; Lyssenko, K. A.; Antipin, M. Yu.; Weber, D.; Bauer, I.; Habicher, W. D.; Nifantyev, E. E. Cyclophosphorylation of polyphenols by diamidoaryl phosphites. Tetrahedron 2003, 59, 1753-1761.
21. Maslennikova, V. I.; Merkulov, R. V.; Vasyanina, L. K.; Bauer, I.; Weber, D.; Theumer, G.; Habicher, W. D.; Nifantyev, E. E. Approaches to the synthesis of conjugates of phosphocavitands and natural compounds. Phosphorus, Sulfur Silicon. 2003, 178, 1-17.
22. Nifantyev, E. E.; Maslennikova, V. I.; Merkulov, R. V.; Lysenko, R. A.; Antipin, M. Yu. The first example of the supramolecular regulation of amidophosphite reactivity. Mendeleev Commun. 2000, 195-196.
23. Burilov, A. R.; Nikolaeva, I. L.; Galimov, R. D.; Pudovik, M. A.; Reznik, V. S. Novel P(III)-phosphorylated Cavitands. Zh. Obshch. Khim. 1995, 65, 1745-1746.
24. Konovalov, A. I.; Reznik, V. S.; Pudovik, M. A.; Kazakova, E. Kh.; Burilov, A. R.; Nikolaeva, I. L.; Makarova, N. A.; Davlescina, G. R.; Ermolaeva, L. V.; Galimov, R. D.; Mustafina, A. R. Synthesis of new phosphorus-containing three-dimensional structures of the basis of calix[4]resorcinarenes. Phosphorus, Sulfur Silicon. 1997, 123, 277-292.
25. Makarova, N. A.; Kazakova, E. Kh.; Zotkina, V. V.; Konovalov, A. I. Phosphorylation of Calix[4]resorcinolarenes with Menthyl Tetraethylphosphorodiamidite and 1,2:5,6-Di-O-isopropylideneglucofuranosyl Tetraethylphosphorodiamidite. Russ. J. Gen. Chem. 1998, 68, 876-880.
26. Kazakova, E. Kh.; Makarova, N. A.; Zotkina, V. V.; Burilov, A. R.; Pudovik, M. A.; Konovalov, A. I. Interaction of resorcinol-octanal cyclotetramer with bis(N,N-diethylamido)menthylphosphite. Mendeleev Commun. 1996, 157-159.
27. Nifantiev, E. E.; Grachev, M. K.; Burmistrov, S. Yu. Amides of Trivalent Phosphorus Acids as Phosphorylating Reagents for Proton-Donating Nucleophiles. Chem. Rev. 2000, 100, 3755-3799.
28. Neda, I.; Kaukorat, T.; Schmutzler, R. Functionalization of the periphery of calix[4]arenes and calix[4]resorcinarenes with phosphorus-containing substituents. Main Group Chem. News 1998, 6, 4-29.
29. Antipin, I. S.; Kazakova, E. Kh.; Habicher, W. D.; Konovalov, A. I. Phosphorus-containing calixarenes. Russ. Chem. Rev. 1998, 67, 905-922.
30. Nifantyev, E. E.; Maslennikova, V. I.; Rasadkina, E. N. New Phosphorus-Containing Cavity Systems. Russ. J. Gen. Chem. 1999, 69, 1736-1758.
31. Shkarina, E. V.; Maslennikova, V. I.; Vasyanina, L. K.; Lyssenko, K. A.; Antipin, M. Yu.; Nifantyev, E. E. Phosphocavitands. II. Synthesis of P(V) Phosphocavitands by Oxidation of P(III) Phosphocavitands. Stereoselectivity of the Process. Russ. J. Gen. Chem. 1997, 67, 1867-1874.
32. Bibal, B.; Tinant, B.; Declercq, J. P.; Dutasta, J. P. A new supramolecular assembly obtained from the combination of silver(1) cations with a thiophosphorylated cavitand. Chem. Commun. 2002, 432-433.
33. Bibal, B.; Declercq, J. P.; Dutasta, J. P.; Tinant, B.; Valade, A. G. Thiophosphorylated cavitand: structure and affinity towards soft metal ions. Tenrahedron 2003, 59, 31 5849-5854.
34. Maslennikova, V. I.; Goryukhina, S. E.; Vasyanina, L. K.; Nifantyev, E. E. Selective oxidative imination of Phosphocavitands. Phosphorus, Sulfur Silicon 2001, 177, 1-4.
35. Sinicina, T. K.; Maslennikova, V. I.; Vasyanina, L. K.; Dyagileva, M. V.; Nifantyev, E. E. Phosphocavitands: III. Alkylation of P(III) Phosphocavitands. Russ. J. Gen. Chem. 2000, 70, 714-720.
36. Nifantyev, E. E.; Maslennikova, V. I.;Sinicina, T. K.; Serkova, O. S. Reaction of Phosphoramidite Cavitands with Derivatives of tetrafluoroboric acid. Russ. J. Gen. Chem. 2000, 70, 640-641.
37. Xu, W.; Rourke, J. P.; Vittal, J. J.; Puddephatt, R. J. Anion Inclusion by a Calix[4]arene Complex: a Contrast between Tetranuclear Gold (I) and Copper (I) Complexes. J. Chem. Soc., Chem. Commun. 1993, 145-147.
38. Xu, W.; Rourke, J. P.; Jagadese, J.; Vittal, J. J.; Puddephatt, R. J. Transition Metal Rimmed-Calixresorcinarene Complexes. Inorg. Chem. 1995, 34, 323-329.
39. Xu, W.; Vittal, J. J.; Puddephatt, R. J. Inorganic Inclusion Chemistry: A Novel Anion Inclusion System. J. Am. Chem. Soc. 1995, 117, 8362-8371.
40. Sakhaii, P.; Neda, I.; Freytag, M.; Thonnessen, H.; Jones, P. G.; Schmutzler, R. Stereoselective Synthesis and Structure of New Types of Calix[4]resorcinarenes. Complexation of Tetrakis(O, O-Phosphorus)-Bridged- Calix[4]resorcinarenes with Heavy Metal Atoms. Z. Anorg. Allg. Chem. 2000, 626, 1246-1254.
41. Maslennikova, V. I.; Serkova, O. S.; Vasyanina, L. K.; Lyssenko, K. A.; Antipin, M. Yu.; Nifantyev, E. E. First heterobimetallic complexes of Phosphocavitands. J. Organomet. Chem. 2003, 677, 21-27.
42. Nifantyev, E. E.; Maslennikova, V. I.; Goryukhina, S. E.; Vasyanina, L. K.; Lyssenko, K. A.; Antipin, M. Yu. Synthesis and structural peculiarities of tetranuclear rhodium complexes of amidophosphito- and phosphitocavitands. Izv. Ross. Akad. Nauk, Ser. Khim. 1998, 1852-1858.
43. Maslennikova, V. I.; Goryukhina, S. E.; Vasyanina, L. K.; Nifantyev, E. E. Complexes of Phosphocavitands with Group VI Metals. Phosphorus, Sulfur Silicon 2000, 164, 61-66.
44. Nifantyev, E. E.; Maslennikova, V. I.; Goryukhina, S. E.; Antipin, M. Yu.; Lyssenko, K. A.; Vasyanina, L. K. Complexes of P(III)-Phosphocavitands with Group VI and VII Transition Metal Carbonyls. J. Organomet. Chem. 2001, 631, 1-8.
45. Maslennikova, V. I.; Goryukhina, S. E.; Serkova, O. S.; Vasyanina, L. K.; Nifantyev, E. E. Bimetallic complexes of amidophosphitocavitands. Russ. J. Gen. Chem. 2002, 72, 816-817.
46. Irico, A.; Vincenti, M.; Dalcanale, E. Diastereoselective Formation of Host-Guest Complexes between a Series of Phosphate-Bridged Cavitands and Alkyl- and Arylammonium Ions Studied by Liquid Secondary-Ion Mass Spectrometry. Chem. - Eur. J. 2001, 7 (9), 2034-2042.
47. Dutasta, J. P.; Bibal, B.; Delange, P.; Gosse, I.; Mulatier, J. C. Synthesis, host properties and structure of phosphorylated cavitands. Phosphorus, Sulfur Silicon 1999, 144/146, 337-341.