Hochphenylierte Benzol‐carbonsäuren und ihre Umwandlungsprodukte (Hocharylierte, III. Mitteil.)

Dilthey, W.; Thewalt, I.; Trösken, O.

doi:10.1002/cber.19340671203

Cited by 31 publications

(9 citation statements)

References 2 publications

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“…Elution with a mixture of light petroleum and dichloromethane (1/1) produced a faint yellow band that was not collected, followed by the recovered tetracyclone. Elution with dichloromethane afforded a yellow band of organic material (IR 1741 cm –1 ), identified as a mixture of dimethyl tetraphenylphthalate (by comparison with an authentic sample prepared from DMAD and tetracyclone in refluxing toluene) and hexamethyl mellitate . Elution with a mixture of CH 2 Cl 2 and acetone (99/1) separated a small yellow-brown band, and changing to a 95/5 ratio of the same solvents produced the dark green zone due to [Mo(CO)(RCCR)(η 5 ,σ-C 4 Ph 4 COCRCR)].…”

Section: Methodsmentioning

confidence: 99%

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Reactions of Tetracyclone Molybdenum Complexes with Electrophilic Alkynes: Cyclopentadienone–Alkyne Coupling and Alkyne Coordination

et al. 2017

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The reactions of the complexes [Mo(CO) 2 (8); on replacing the π-acceptor carbonyl ligand by the π-donor oxo group, the alkyne ligand changes orientation: it lies parallel to the MoÐ CO bond in 3 but perpendicular to the Mo=O group in 8. Analogous complexes (9, 10) were isolated in the case of methyl propiolate; each exists as a mixture of two isomers depending on the orientation of the unsymmetrical alkyne ligand.

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Section: Methodsmentioning

confidence: 99%

“…with an authentic sample prepared from DMAD and tetracyclone in refluxing toluene) 29 Ph),120.3,116.0,114.8,109.9 (all CPh), 53.0, 52. 8,52.5,52.2 (all Me …”

Section: Methodsmentioning

confidence: 99%

Reactions of Tetracyclone Molybdenum Complexes with Electrophilic Alkynes: Cyclopentadienone–Alkyne Coupling and Alkyne Coordination

et al. 2017

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“…Chromatography on silica using a gradient of ethyl acetate (5% ¡ 10% ¡ 50%) in pentane yielded 1,2,3,4-tetraphenylfluorenone 14 as a yellow solid (470 mg, 0.97 mmol, 98%), mp 303-304°C (lit. 298°C 59,60 13 …”

Section: Preparation Of 1234-tetraphenylfluorenone (14)mentioning

confidence: 99%

Organic and organometallic derivatives of pentaphenylbenzene, C₆Ph₅X: correlation of peripheral phenyl ring orientations with the steric bulk of “X”

et al. 2013

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A series of C 6 Ph 5 X compounds, including X = H, Br, CO 2 H, CO 2 R, C'CPh, cis-BrC=C(Br)Ph, 2-bornenyl, and ferrocenyl, have been characterized by use of X-ray crystallography. Also, the first organometallic complexes of pentaphenylbenzene have been prepared by reaction with chromium hexacarbonyl to yield ( 6 -C 6 Ph 5 H)Cr(CO) 3 complexes in which the metal tripod is attached either to an ortho peripheral ring or to the central ring. Crystalline pentaphenylbenzoic acid exists as a hydrogenbonded dimer; however, the steric bulk of the substituents does not allow the carboxylic acid moieties to be linked directly but instead via two bridging methanol molecules. In the solid state, the orientation of the peripheral rings in bulky C 6 Ph 5 X systems is very sensitive to the size of the "X" substituents, such that the twist angle of the para ring responds inversely with increasing bulk of "X", which drives the ortho rings farther out of the plane of the central ring. The relevance of these observations to correlated motion in molecular propellers, and ultimately to molecular machines, is discussed.Résumé : À l'aide de la cristallographie aux rayons X, on a caractérisé une série de composés de formule C 6 Ph 5 X, où X = H, Br, CO 2 H, CO 2 R, C'CPh, cis-BrC=C(Br)Ph, 2-bornényl et ferrocényl. En outre, on a préparé les premiers complexes organométal-liques du pentaphénylbenzène en le faisant réagir avec de l'hexacarbonyle de chrome pour obtenir les complexes ( 6 -C 6 Ph 5 H)Cr(CO) 3 dans lesquels le tripode métallique est attaché à un noyau périphérique en ortho ou au noyau central. L'acide pentaphénylbenzoïque existe à l'état de dimère formé par liaisons hydrogènes; toutefois, l'encombrement stérique des substituants ne permet pas la liaison directe des groupements carboxyliques qui sont plutôt reliés par un pont constitué de deux molécules de méthanol. À l'état solide, l'orientation des noyaux périphériques dans les volumineux systèmes C 6 Ph 5 X est très sensible à la taille des substituants « X », de sorte que l'angle de torsion du noyau en para répond inversement à l'encombrement croissant de « X » qui repousse de plus en plus les noyaux en ortho hors du plan du noyau central. Une discussion de l'intérêt de ces observations en ce qui concerne le mouvement corrélé dans les hélices moléculaires, et en bout de ligne les machines moléculaires, est offerte. [Traduit par la Rédaction]

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“…Relatively few cyclopentadienones are known (because they add to themselves, as will shortly become evident), and they are all polyarylated. They are obtained from 1,2-diketones and dibenzyl ketones, a reaction of aldol condensation investigated by Japp (60,62,63) (who, however, never isolated any of the cyclopentadienones) and by Dilthey (37)(38)(39)(40)(41)(42)(43)(44)(45)(46)(47)(48)(49)(50)(51). The most useful has been tetraphenylcyclopentadienone (47, 55); the name has been abbreviated to "tetracyclone" and the class as a whole is sometimes termed "cyclones.…”

Section: Rc=crmentioning

confidence: 99%

Carbonyl Bridge Compounds and Related Substances.

Allen¹

1945

Chem. Rev.

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Hochphenylierte Benzol‐carbonsäuren und ihre Umwandlungsprodukte (Hocharylierte, III. Mitteil.)

Cited by 31 publications

References 2 publications

Reactions of Tetracyclone Molybdenum Complexes with Electrophilic Alkynes: Cyclopentadienone–Alkyne Coupling and Alkyne Coordination

Reactions of Tetracyclone Molybdenum Complexes with Electrophilic Alkynes: Cyclopentadienone–Alkyne Coupling and Alkyne Coordination

Organic and organometallic derivatives of pentaphenylbenzene, C₆Ph₅X: correlation of peripheral phenyl ring orientations with the steric bulk of “X”

Carbonyl Bridge Compounds and Related Substances.

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Hochphenylierte Benzol‐carbonsäuren und ihre Umwandlungsprodukte (Hocharylierte, III. Mitteil.)

Cited by 31 publications

References 2 publications

Reactions of Tetracyclone Molybdenum Complexes with Electrophilic Alkynes: Cyclopentadienone–Alkyne Coupling and Alkyne Coordination

Reactions of Tetracyclone Molybdenum Complexes with Electrophilic Alkynes: Cyclopentadienone–Alkyne Coupling and Alkyne Coordination

Organic and organometallic derivatives of pentaphenylbenzene, C6Ph5X: correlation of peripheral phenyl ring orientations with the steric bulk of “X”

Carbonyl Bridge Compounds and Related Substances.

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Organic and organometallic derivatives of pentaphenylbenzene, C₆Ph₅X: correlation of peripheral phenyl ring orientations with the steric bulk of “X”