Zur Struktur der Fulvene. Eigenschaften Einiger Phenylfulvene

Kresze, G.; Goetz, Horst

doi:10.1002/cber.19570901008

Cited by 31 publications

(12 citation statements)

References 19 publications

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“…Orange crystals, mp 104–105 °C. Lit 31 mp 106.5 °C. 1 H NMR (500 MHz, CDCl 3 ): δ 7.62 (d, J = 8.7 Hz, 2H), 7.18 (s, 1H), 6.85 (d, J = 5.2 Hz, 1H), 6.74 (d, J = 9.0 Hz, 2H), 6.69 (ddd, J = 5.2, 3.6, 1.6 Hz, 1H), 6.52 – 6.45 (m, 1H), 6.37 (dt, J = 5.0, 1.8 Hz, 1H), 6.37 (dt, J = 5.0, 1.8 Hz, 1H), 3.07 (s, 6H).…”

Section: Methodsmentioning

confidence: 99%

An efficient catalytic method for fulvene synthesis

Coşkun

Erden

2011

Tetrahedron

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Section: Methodsmentioning

confidence: 99%

An efficient catalytic method for fulvene synthesis

Coşkun

Erden

2011

Tetrahedron

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“…Crystal structure determination DMAPF was prepared by the classical Thiele synthesis (Thiele, 1900;Thiele & Balhorn, 1906;Kresze & Goetz, 1957;Otter et al, 1979) and recrystallized from hexane. Crystals of DMAPF belong to the monoclinic space group P21/c, as determined by precession photography.…”

Section: Experimental and Computational Methodsmentioning

confidence: 99%

“…Thus, the dipole moment of fulvene was determined to be 1.1 D in benzene solution (Thiec & Wiemann, 1956) and estimated from the dipole moment of 6,6-diphenylfulvene in benzene (Wheland & Mann, 1949) to be 1.2 D, values considerably higher than the 0.42 D value measured in the gas phase. Furthermore, Kresze & Goetz (1957) have determined the dipole moment of p-(dimethylaminophenyl)fulvene (DMAPF) (1) in benzene to be 3.65 D and have estimated a minimum enhancement of 1.14 D relative to the sum of the moments of the fulvene and N,N-dimethylaniline components. The solution dipole moment of DMAPF is also enhanced over a value of 2.8 D calculated by molecular orbital theory (Ikeda, Kawabe, Sakai & Kawasaki, 1989).…”

Section: Introductionmentioning

confidence: 99%

Molecular structure and crystal packing of 6-(p-dimethylaminophenyl)fulvene

Wingert¹,

Staley²

1992

Acta Crystallogr Sect B

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The single-crystal structure of 6-(p-dimethylaminophenyl)fulvene (DMAPF), ClaHlsN, Mr = 197.28, F(000) = 848, at 123 K has been determined and refined from Mo Ka (A = 0.7107 ,~) X-ray data collected up to sin0/a = 0. (13) A 3. The structure was refined using 6459 unique reflections to a final wR of 5.89% with anisotropic temperature factors on non-H atoms, isotropic temperature factors on H atoms, and populations of radial electron density distributions on every atom as variables in the refinement. All reflections were treated as observed. In both molecules of the asymmetric unit the dihedral angle between the benzenoid and fulvene rings is approximately 15 °, whereas pyramidalization at the N atom is 2.5 times greater in one molecule than in the other. The crystal structure is composed of layers parallel to the ab plane with molecules aligned in the c direction. The molecules of each layer pack with their cross-sections forming a herringbone pattern. Comparison of geometric and electronic features of crystalline DMAPF with those derived by molecular orbital calculations indicate enhanced polarization due to the crystal field.

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“…Die Lösungsmittel wurden nach üblichen Verfahren getrocknet und unter Argon de stilliert, deuterierte Solventien entgast und mit Ar gon gesättigt. Die Synthese von Bis(tetrahydrofuran-0)calcium - [10,11] und Bis(tetrahydrofuran)bariumbis[bis(trimethylsilyl)amid] [9], Bis[bis(trimethylsilyl)-amino]stannylen [13] und 6-Methyl-6-phenylfulven [14] erfolgte entsprechend den Literaturvorschriften. Bei der Interpretation des an einer Nujolverreibung zwischen CsBr-Scheiben an dem IR-Spektrophotometer Paragon 1000PC der Firma Perkin-Elmer angefertigten Schwin gungsspektrums blieben die von Nujol überlagerten Ban den unberücksichtigt (Abschätzung der Intensität: vs sehr stark, s stark, m mittelstark, w schwach, sh Schulter, br breit).…”

Section: Allgem Einesunclassified

Synthese von Erdalkalimetallocenen aus Erdalkalimetall- bis[bis(trimethylsilyl)amid] und 6-Methyl-6-phenylfulven / Synthese von Erdalkalimetallocenen aus Erdalkalimetallbis[ bis(trimethylsilyl)amid] und 6-Methyl-6-phenylfulven Synthesis of Alkaline Earth Metallocenes from Alkaline Earth Metal Bis[bis(trimethylsilyl)amide] and 6 -Methyl-6 -phenylfulvene

Westerhausen

Hartmann

Makropoulos

et al. 1998

Zeitschrift Für Naturforschung B

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The transmetalation of bis[bis(trimethyIsilyl)amino]stannylene in tetrahydrofuran with the alkaline earth metals yields the bis(tetrahydrofuran) adducts of calcium (la), strontium (lb ) and barium bis[bis(trimethylsilyl)amide] (lc). The metalation of 6-methyl-6-phenylfulvene with la, lb and lc gives l,l'-bis(l-phenyl-ethen-l-yl)calcocene 2a, -strontocene 2b and -barocene 2c, respectively. The reaction of lb with equimolar amounts of 6-methyl-6-phenylfulvene and acetophenone leads to the formation of bis[^-[ry5-l-(3 -h y d ro x y -1 -methyl-1,3-dipheny 1-2-propen-1-yl )-2,4-cyclo -pentadien-l-yl](2-)-C ,O :O ]tetrakis(tetrahydrofuran-0)distrontium 3. The metathesis reaction of 2a with YC13 and SnCl2 yields the corresponding yttrocenechloride 4 and stannocene 5. Crystallographic data of la: monoclinic, P 2 , /c, a = 841.6(4), b = 1936.9(6), c= 1938.0(10) pm, ß = 100.84(4)°, Z = 4, wR-> =0,1199); lb: orthorhombic, Pbca, a = 1924.8(4), b = 1747.8(3), c = 1930.1(4) p m ,Z = 8, w/?2 = 0.1248; 3: monoclinic, P2,/c, a = 1230.42(11), b = 1343.08(11), c = 1597.34(14) pm, ß = 104.610(7)°, Z = 4, wR 2 = 0.0980.Wegen der präparativ leichten Zugänglichkeit der schweren Erdalkalimetall-bis[bis(trimethylsilyl)amide] [1] steht derzeit die Reaktivität die ser Verbindungen im Mittelpunkt des Interes ses zahlreicher Arbeitsgruppen [2]. Seit der Kristallstrukturbestimmung des polymeren Calcocens durch Stucky und Zerger [3] wurde besonders das Gebiet der Erdalkalimetallocene intensiv er forscht [4], Generell erhöhen Substituenten am Cyclopentadienid-Liganden die Löslichkeit der Verbindungen. Die Umsetzung von in Ammoniak gelöstem Metall oder von Erdalkalimetall-bis[bis-(trimethylsilyl)amid] mit substituierten Cyclopentadienen führt in guten Ausbeuten zu den Erdal-* Sonderdruckanforderungen an Prof. Dr. M. Westerhausen. kalimetallocenen. In jüngster Zeit bemühen sich Hanusa und Mitarbeiter [5] um die Synthese von Metallocenen mit Donoratome enthaltenden Alkyl substituenten, wobei die entsprechend substituier ten Cyclopentadiene als Edukte eingesetzt wer den. Bei der von uns in Tetrahydrofuran durch geführten Reaktion von Calcium-bis[bis(trimethylsilyl)amid] mit 6 -Methyl-6 -phenylfulven konnte in guten Ausbeuten l,l'-B is(l-phenylethen-l-yl)-calcocen [6 ] isoliert werden. Eine durch die Alkenylbildung hervorgerufene oder sich vergrößern de Ringspannung bei der Verwendung von 6 ,6 -Bis(cyclopropyl)fulven verlängert die Reaktions zeiten beträchtlich [7]. Die Molekülstrukturen der als Edukte verwende ten Bis(tetrahydrofuran)magnesium-[8] und Bis(tetrahydrofuran)barium-bis[bis(trimethylsilyl)-amide] [9] wurden bereits publiziert, während

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Zur Struktur der Fulvene. Eigenschaften Einiger Phenylfulvene

Cited by 31 publications

References 19 publications

An efficient catalytic method for fulvene synthesis

An efficient catalytic method for fulvene synthesis

Molecular structure and crystal packing of 6-(p-dimethylaminophenyl)fulvene

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