Synthesis, Structure, and Reactivity of Tetrakis(<i>O,O</i>‐phosphorus)‐Bridged Calix[4]resorcinols and Their Derivatives

Vollbrecht, Alexander; Neda, Ion; Thönnessen, Holger; Jones, Peter G.; Schmutzler, Reinhard; Harris, Robin K.; Crowe, Lindsey A.

doi:10.1002/cber.19971301124

Cited by 38 publications

(30 citation statements)

References 24 publications

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“…The reaction of the tetrakis-(O,O-phosphorus)-bridged-calix [4]resorcinarene 13 [14] with CuCl in moist CH 3 CN did not yield the expected, analogous organized atomic framework 14 (Scheme 3). The complexation reaction was performed at room temperature and afforded the known anionic atomic framework of 14.…”

Section: D) Preparation Of 14 and 15mentioning

confidence: 82%

“…The progress of the complexation reaction has been followed by 31 P-NMR spectroscopy. The reaction of 13 [14] with (tht)AuCl in CH 2 Cl 2 at room temperature furnished the complex 15 in quantitative yield. The latter was identified by 1 H-, 31 P-NMR spectroscopy and elemental analysis.…”

Section: D) Preparation Of 14 and 15mentioning

confidence: 98%

“…It has been recognized that the tetrakis-(O,O-phosphorus)-bridged-calix [4]resorcinarene 13 [14] possesses good solubility in most organic solvents and is suitable to act as a ligand in complexation reactions. The progress of the complexation reaction has been followed by 31 P-NMR spectroscopy.…”

Section: D) Preparation Of 14 and 15mentioning

confidence: 99%

“…The stereochemistry of 4 was elucidated by an X-ray crystallographic analysis of the octaacetate derivative 5. The complexation of the tetrakis(O,O-phosphorus)-bridged calix [4]resorcinarene (13) [14] with (tht)AuCl (tht = tetrahydrothiophene) and CuCl led to the formation of compounds 14 and 15 in quantitative yield. The structure of the complexes 14 and 15 was confirmed by X-ray crystallographic analysis and a study of the symmetry considerations of compounds 14 and 15 is presented.…”

Section: Introductionmentioning

confidence: 98%

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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

Sakhaii

Neda

Freytag

et al. 2000

Z. anorg. allg. Chem.

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The acid‐catalyzed (with HCl) condensation reactions of resorcinol (1) with 1‐naphthaldehyde (2) and isobutyraldehyde (3) furnished the tetrameric macrocyclic compounds 4 and 6. Detailed NMR‐investigations of the acetylated tetrameric species 5 surprisingly support a structure not in agreement with the expected all‐cis conformation. The chair conformation (C2h symmetry) of the acetylated derivative 5 was established through a crystal X‐ray diffraction study. The naphthyl substituents are arranged in trans position above and below the plane made up by the resorcinol units. The reaction of resorcinol 1 with isobutyraldehyde, in accord with expectation, led to the calix[4]resorcinaren (6). The 1H NMR spectra of compound 6 and 7 appeared at room temperature as broad signals, indicating a conformation of C2v symmetry. The reaction of the C‐methyl‐tetrakis‐P‐(chlorodioxaphosphocin)‐calix[4]resorcinarenes (8) and (10) with suitable N‐trimethylsilyl organic amines were conducted in tetrahydrofuran suspension, furnishing the P–N‐substituted calix[4]resorcinarenes (9) and (11). While in the complexation of C‐methyl‐tetrabromotetrakis‐P‐(dimethylaminodioxaphosphocin)‐calix[4]resorcinarene (13) with (tht)AuCl (tht = tetrahydrothiophene) the expected, neutral tetra‐substituted complex 15 was formed, the reaction of 13 with moist acetonitrile led to the anionic atomic framework 14. X‐ray structure determinations of the complexes 14 and 15 show that both possess the cone conformation. In the gold complex 15, the Au–Cl groups form a loose aggregate, with three Au…Cl contacts of 316–340 pm; one of the groups points towards the centre of the cone. The copper(I) complex 14 displays crystallographic mirror symmetry, with a central Cu4Cl5 unit involving tetrahedrally coordinated copper.

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Section: D) Preparation Of 14 and 15mentioning

confidence: 82%

Section: D) Preparation Of 14 and 15mentioning

confidence: 98%

Section: D) Preparation Of 14 and 15mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 98%

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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

Sakhaii

Neda

Freytag

et al. 2000

Z. anorg. allg. Chem.

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“…The 31p NMR spectra (32. (2) 3823(I) 6378(1) 6411(l) 39(1) Rh (3) 133(I) 6313(1) 5516(I) 53(I) Rh (4) 3828(11 1157(I) 7076(1) 41(11 P(I) 6600(I) 1994(11 8795(I) 35(11 P (2) 4023(I) 6685(11 7375(I) 37(t) P (3) 57 (1) 5586(1) 6688(l) 40(I) P (4) 2983 (1) 701(I) 8002(I) 37(I) 0 (1) 6221 (2) 1193 (2) 9437 (2) 35 (1) 0(2) 6453 (2) 2809 (2) 9099 (2) 38 (11 0(3) 7696 (2) (2) 40(11 0 (6) 4440 (3) 7551 (2) 7283 (2) 47 (11 0(7) 189 (3) 6173 (2) 7164(21 44(!) 0 (8) 843 (3) 4629 (2) 7064 (2) 43(I) 0 (9) -928 (3) 5380 (3) (2) 32(11 C (7) 3318 (4) 5657 (3) (32) 4788 (4) 215t (4) 10929 (3) 42(1/ C (33) 8447 (4) 1987 (4) 8739 ( (5) sl02 (5) 6562 (3) 59(2) C(40) -2404 (6) 5890 (6) 6190(51 98(3) C(41) -1825(61 4268 (5) 7119 (4) 73 (2)…”

Section: Methodsunclassified

Synthesis and structural features of tetranuclear rhodium complexes of amidophosphito- and phosphitocavitands

et al. 1998

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Interactions of acetylacetonatodicarbonylrhodiumO) with amidophosphito-and phosphitocavitands were studied. First representatives of tetranuclear cavity complexes of rhodium(I) were obtained. It was established by NMR spectroscopy and X-ray diffraction studies that the chemically identical phosphorhodium centers in these complexes differ in the spatial arrangement, and the system as a whole becomes unsymmetrical.

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Synthesis and Binding Properties of iiii (4i) Stereoisomers of Phosphonato Cavitands − Cooperative Effects in Cation Complexation in Organic Solvents

et al. 2001

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Syntheses and host-guest properties of tetrabridged phosphorylated cavitands in their iiii (4i) configurations are described. The tetraphosphonato cavitands 2 and 3, with the four P=O bonds oriented inwards (4i stereoisomer) were prepared in 25% and 53% yields respectively, from the corresponding resorc[4]arenes, dichloro(phenyl)phosphane oxide and base. The formation of the 4i stereoisomers is solventdependent and is attributable to the capability of an ammonium guest to form an inclusion complex. Only the iiio (3io) stereoisomer of 3 was isolated otherwise, in low yield. These phosphonato cavitands, in their 4i configurations, are particularly efficient extractants for metal ions. The free energies of complexation of 3 with alkali metal and ammonium cations

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Synthesis, Structure, and Reactivity of Tetrakis(O,O‐phosphorus)‐Bridged Calix[4]resorcinols and Their Derivatives

Cited by 38 publications

References 24 publications

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

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

Synthesis and structural features of tetranuclear rhodium complexes of amidophosphito- and phosphitocavitands

Synthesis and Binding Properties of iiii (4i) Stereoisomers of Phosphonato Cavitands − Cooperative Effects in Cation Complexation in Organic Solvents

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