Tetraphenylarsonium 1,2,3,4,5-pentakis(methylmercapto)cyclopentadienide

Wudl, Fred; Nalewajek, D.; Rotella, F. J.; Gebert, E.

doi:10.1021/ja00409a044

Cited by 21 publications

(13 citation statements)

References 6 publications

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“…Charged persulfurated aromatic compounds include the cyclopentadienyl anion and the cyclopropenyl cation. In an attempt to prepare organic conductors, pentakis(methylthio)cyclopentadiene anions were produced in 198150 by reacting sodium cyclopentadienyl with NaH and dimethyl disulfide (Scheme ). Other substituted cyclopentadienes with methylthio‐ or arylthio‐ groups were also reported 51.…”

Section: Synthesis Scope and Mechanistic Insightmentioning

confidence: 99%

“…Interestingly and unexpectedly, the pentakis(methylthio)cyclopentadienyl anion ( 57 ) exhibited an aaaab pattern (Figure 16). 50…”

Section: Conformation and X‐ray Crystallographymentioning

confidence: 99%

“… ORTEP plot of the pentakis(thiomethyl)cyclopentadienyl anion ( 57 ; 50 % probability ellipsoids for thiomethyl groups). Reproduced, with permission, from reference 50. …”

Section: Conformation and X‐ray Crystallographymentioning

confidence: 99%

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Persulfurated Aromatic Compounds

2006

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Persulfurated arenes have been known for about 50 years but they were underexploited in chemistry in spite of facile, mild, and high-yielding syntheses. Their properties (redox potentials, UV/Vis absorption, conductivity, nonlinear optical properties, etc.) are mainly due to the aromaticity of the ring with sp2-hybridized carbon atoms and to the electronic contribution from numerous divalent sulfur ligands, which also stabilize negative or positive charges. The characteristic conformational patterns of the sulfur ligands often facilitate preorganization in supramolecular assemblies, with or without thiophilic metal cations, for designing redox sensors, ion-selective membranes, clathrates, organic conductors, nonlinear optical materials, liquid crystals, coordination polymers, and bioinorganic systems. A new class of supramolecules with various molecular shapes such as asterisks, chains, wheels, and windmills were reported.

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Section: Synthesis Scope and Mechanistic Insightmentioning

confidence: 99%

“…Interestingly and unexpectedly, the pentakis(methylthio)cyclopentadienyl anion ( 57 ) exhibited an aaaab pattern (Figure 16). 50…”

Section: Conformation and X‐ray Crystallographymentioning

confidence: 99%

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Persulfurated Aromatic Compounds

2006

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“…Bei Verwen dung der Elektrophile C 0 2 und PPh2Cl entstehen nun die entsprechenden unsymmetrischen und d a mit chiralen funktioneilen Bisthioether 6 a und 7 a,b . Wie schon 3 a läßt sich auch 6 a in die C arbon säure 6 b und das Säurechlorid 6 c überführen. Die beiden Thioether-Phosphane 7 a und 7 b enthalten nun im Unterschied zu 4 zwangsläufig eine SRund eine PPh2-Gruppe in benachbarter Position.…”

Section: Kristallstrukturanalyse Von 7 Aunclassified

“…Dies gilt in besonderem M aße für funktionelle Substi tuenten mit freien Elektronenpaaren mit D onor eigenschaften für ein Metallion, da bei der übli chen Synthese der Metallocene aus Metallsalz und (funktionalisiertem) Cyclopentadienid [2] bei sol chen Systemen bevorzugter Angriff des Metallions an der funktionellen G ruppe und nicht am ^-Sy stem des Cyclopentadienylrings erfolgt [6,7], Der alternative Reaktionsweg, die nachträgliche Funktionalisierung bereits ^-koordinierter Cyclopentadienyl-Liganden war bis vor wenigen Jahren auf solche Systeme beschränkt, die die drastischen Re aktionsbedingungen einer Friedel-Crafts-Acylie-* Sonderdruckanforderungen an Dr. Karlheinz Sünkel.…”

Section: Introductionunclassified

Koordinationschemie perhalogenierter Cyclopentadiene und Alkine, XI [1].<br />Darstellung einiger Cymantrenyl-mono- und bis-thioether mit einer weiteren funktionellen Gruppe am Cyclopentadienylring. Molekülstruktur von [C₅Cl₂(SMe)₂(PPh₂)]Mn(CO)₃ / Coordination Chemistry of Perhalogenated Cyclopentadienes and Alkynes, XI [1]<br />Synthesis of Some Cymantrene Mono- and Bis-Thioethers with One Additional Functional Group on the Cyclopentadieny

Sünkel¹,

Blum²,

Wagner³

1993

Zeitschrift Für Naturforschung B

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M ultifunctional Cymantrene Thioethers, Organometallic P -S -C h elate Ligand, Chiral Cyclopentadienyl Complexes, Crystal StructureThe reaction o f [C5Cl4(SM e)]M n(CO)3 (la ) with «-butyllithium and the electrophiles SiM e3Cl, C 0 2, or PPh,Cl regiospecifically yields the chiral 1, , 7 a , Ph, 7b) can be obtained. The crystal structure determination o f 7a (C " H 160 3PS-,CLMn, m onoclinic, P 2,/c, a = 18.714(6) A, b = 9.506(3) A, c = 14.475(3) A, ß = 109.18(2)°, V = 2432.1(12) A \ Z = 4) shows an orientation o f the neighbouring PPh2-and SMe groups, that allows chelation o f an additional metal fragment. 3-disubstituted functional cym an trene thioethers [C5Cl3(SM e)R]M n(CO )3 (R = SiM e3 (2), COOLi (3a), PPh2 (4)). 3 a can be protonated to give the corresponding carboxylic acid (3 b), which in turn can be transformed to the acid chloride [C5Cl3(SM e)(COCl)]M n(CO)3 (3c). 3c reacts with N a N 3 to yield after work-up the urea derivative O C [[N H -C 5Cl3(SM e)]M n(CO)3]2 (3d). U sing the cymantrene bisthioethers [C5Cl3(SR )2]M n(CO)3 (R = Me, 5a, Ph, 5b) as starting materials, the carboxyl de rivatives [C5Cl2(SM e)2(COR)]M n(CO)3 (R = OLi, 6a, OH, 6b, Cl, 6 c) and the potential organometallic S,P-chelate ligands [C5Cl2(SR)2(PPh2)]M n(CO)3 (R = Me

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