Functionalization of the periphery of calix[4]resorcinarenes with P(III)-containing substituents via hydroxy, trimethylsiloxy, and ethoxy-tethered trimethylsiloxy intermediates

Neda, Ion; Vollbrecht, Alexander; Grunenberg, Jörg; Schmutzler, Reinhard

doi:10.1002/(sici)1098-1071(1998)9:6<553::aid-hc5>3.0.co;2-5

Cited by 8 publications

(29 citation statements)

References 6 publications

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“…Our efforts were concerned mainly with the design and study of calix [4]arenes and calix [4]resorcinarenes bearing two or four P(III) or P(V) ligands tethered at distal phenol units [4,5]. Thus, we have reported the synthesis of a wide variety of calix [4]arenes containing trivalent phosphorus groups and their application to the hydroformylation of 1-octene [6], although we did not know the exact nature of the catalysts formed in situ.…”

Section: Introductionmentioning

confidence: 99%

“…Thus, we have reported the synthesis of a wide variety of calix [4]arenes containing trivalent phosphorus groups and their application to the hydroformylation of 1-octene [6], although we did not know the exact nature of the catalysts formed in situ.…”

Section: Introductionmentioning

confidence: 99%

“…Because of the broad tunability and variability mentioned above, calix [4]arenes with phosphorus-containing groups as ligands should have an interesting potential for selective hydroformylation reactions. As recently shown, bidentate bisphosphites with a calix [4]arene backbone can advantageously be used in the Rh(I)-catalyzed hydroformylation of 1-octene at low pressure, affording a good n/iso ratio [7].…”

Section: Introductionmentioning

confidence: 99%

“…As recently shown, bidentate bisphosphites with a calix [4]arene backbone can advantageously be used in the Rh(I)-catalyzed hydroformylation of 1-octene at low pressure, affording a good n/iso ratio [7]. Various studies have described the application of phosphorus-containing platinum complexes as catalysts in the hydroformylation of styrene [8Ϫ10].…”

Section: Introductionmentioning

confidence: 99%

“…In the present study, we describe a synthetic method leading to transition metal chelate complexes starting from calix [4]arenes containing 1,3,5-triaza-2σ 3 λ 3 -phosphorin-4,6-dionyloxy groups with [(cod)RhCl] 2 , (cod)Rh(acac), (nbd)Rh(acac) and (cod)PtCl 2 complexes (acac ϭ acetylacetonato, cod ϭ cycloocta-1,5-diene, nbd ϭ norbornadi-* Prof. Dr. R. Schmutzler Institut für Anorgan. und Analyt.…”

Section: Introductionmentioning

confidence: 99%

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Mono- and Binuclear Rhodium and Platinum Complexes of 1, 3, 5-Trimethyl-1, 3, 5-triaza-2σ3λ3-phosphorin-4, 6-dionyloxy-substituted Calix[4]arenes

Kunze

Neda

Freytag

et al. 2002

Z. anorg. allg. Chem.

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The reaction behaviour of 1,3,5-triaza-2σ 3 λ 3 -phosphorin-4,6-dionyloxy-substituted calix[4]arenes towards mono-and binuclear rhodium and platinum complexes was investigated. Special attention was directed to structure and dynamic behaviour of the products in solution and in the solid state. Depending on the molar ratio of the reactands, the reaction of the tetrakis(triazaphosphorindionyloxy)-substituted calix[4]arene (4) and its tert-butyl-derivative (1) with [(cod)RhCl] 2 yielded the mono-and disubstituted binuclear rhodium complexes 2, 3, and 5. In all cases, a C 2 -symmetrical structure was proved in solution, apparently caused by a fast intramolecular exchange process between cone conformation and 1,3-alternating conformation. The X-ray crystal structure determination of 5 confirmed [(calixarene)RhCl] 2 -coordination through two opposite phosphorus atoms with a P····P separation of 345 pm. The complex displays crystallographic inversion symmetry, and the Rh 2 Cl 2 core is thus exactly planar. Reaction of 1 and of the bis(triazaphosphorindionyloxy)-bis(methoxy)-substituted tert-butyl-calix-[4]arene (7) with (cod)Rh(acac) in equimolar ratio and subsequent reaction with HBF 4 led to the expected cationic monorhodium Ein-und zweikernige Komplexe des Rhodiums und Platins von 1,3,5-Trimethyl-1,3,5-triaza-2σ 3 λ 3 -phosphorin-4,6-dionyloxy-substituierten Calix[4]arenen Inhaltsübersicht. Das Reaktionsverhalten von 1,3,5-Trimethyl-1,3,5-triaza-2σ 3 λ 3 -phosphorin-4,6-dionyloxy-substituierten Calix-[4]arenen gegenüber ein-und zweikernigen Rhodium-und PlatinKomplexen wurde untersucht. Besonderes Augenmerk wurde auf die Untersuchung der Struktur und des dynamischen Verhaltens der Produkte im festen Zustand und in Lösung gelegt. Abhängig vom molaren Verhältnis der Reaktanden lieferte die Umsetzung des tetrakis(triazaphosphorindionyloxy)-substituierten Calix[4]-arens (4) und seines tert-Butyl-Analogons (1) mit [(cod)RhCl] 2 die mono-und disubstituierten, zweikernigen Rhodiumkomplexe 2, 3 und 5. In allen Fällen wurde eine C 2 -symmetrische Struktur in Lö-sung nachgewiesen, die anscheinend aus einem schnellen intramolekularen Austauschprozeß zwischen der Konus-und der 1,3-alternierenden Konformation resultiert. Die Röntgenstrukturana-lyse von 5 bestätigte die [(Calixaren)RhCl] 2 -Koordination über zwei gegenüberliegende Phosphoratome mit einem P····P-Abstand von 345 pm. Der Komplex zeigt kristallographische Inversionssymmetrie, damit ist die Rh 2 Cl 2 -Verbrückungseinheit exakt planar. Die Reaktion von 1 und dem bis(triazaphosphorindionyloxy)-bis(methoxy)-substituierten tert-Butyl-Calix[4]aren (7) mit (cod)-Rh(acac) in äquimolarem Verhältnis und anschließender Umsetcomplexes 6 and 8, involving 1,3-alternating P-Rh-P-coordination. The cone conformation in solution was proved by NMR spectroscopy and characteristic values of the 1 J(PRh) coupling constants in the 31 P-NMR-spectra. Reaction of equimolar amounts of 4 with (cod)Rh(acac) or (nbd)Rh(acac) led, by substitution of the labile coordinated acetylacetonato and after a...

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Mono- and Binuclear Rhodium and Platinum Complexes of 1, 3, 5-Trimethyl-1, 3, 5-triaza-2σ3λ3-phosphorin-4, 6-dionyloxy-substituted Calix[4]arenes

Kunze

Neda

Freytag

et al. 2002

Z. anorg. allg. Chem.

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Molecular Recognition and Host–Guest Interactions

Haiduc

Edelmann

1999

Supramolecular Organometallic Chemistry

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Macrocyclic organomercury compounds have been known for some time, but their ability to bind anionic guests in their cavity was demonstrated relatively recently. This molecular recognition process is somewhat similar to the formation of the crown ether complexes, except that the binding sites of the macrocycle are occupied by metal atoms, able to function as Lewis acids, and therefore to bind halogen and other Lewis base anions. This approach is only in its beginnings and the recent discovery of mercuracarbaboranes as anion binding cyclic receptors gave a new impetus to research in the field.One of the earliest known organomercury macrocycles was the trimer of ovthophenylene mercury, (o-CgH4Hg)3, known from X-ray diffraction studies to have a planar cyclic structure, 1 [I, 21. It has recently been found, with the aid of 199Hg NMR spectroscopy, that this compound forms complexes with halide anions (Cl-, Br-and I-) in dichloromethane solution, but the complexes could not be isolated in solid state [3]. The fluorinated analog (o-CgF4Hg)3, 2, is a much better electron acceptor and forms stable complexes with the same halide anions; these could be 1 2 2.

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ChemInform Abstract: Functionalization of the Periphery of Calix[4]resorcinarenes with P(III)‐Containing Substituents via Hydroxy, Trimethylsiloxy, and Ethoxy‐Tethered Trimethylsiloxy Intermediates.

et al. 1998

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Functionalization of the periphery of calix[4]resorcinarenes with P(III)-containing substituents via hydroxy, trimethylsiloxy, and ethoxy-tethered trimethylsiloxy intermediates

Cited by 8 publications

References 6 publications

Mono- and Binuclear Rhodium and Platinum Complexes of 1, 3, 5-Trimethyl-1, 3, 5-triaza-2σ3λ3-phosphorin-4, 6-dionyloxy-substituted Calix[4]arenes

Mono- and Binuclear Rhodium and Platinum Complexes of 1, 3, 5-Trimethyl-1, 3, 5-triaza-2σ3λ3-phosphorin-4, 6-dionyloxy-substituted Calix[4]arenes

Molecular Recognition and Host–Guest Interactions

ChemInform Abstract: Functionalization of the Periphery of Calix[4]resorcinarenes with P(III)‐Containing Substituents via Hydroxy, Trimethylsiloxy, and Ethoxy‐Tethered Trimethylsiloxy Intermediates.

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