Tribenzocyclyne (TBC) and Tetrabenzocyclyne (QBC)

Solooki, D.; Ferrara, Joseph D.; Malaba, Dennis; Bradshaw, J. D.; Tessier, Claire A.; Youngs, Wiley J.; John, J. A.; Tour, James M.

doi:10.1002/9780470132623.ch19

Cited by 25 publications

(17 citation statements)

References 17 publications

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“…Because of the discovery of simple and more efficient catalytic sp cross-coupling procedures, the Stephens-Castro reaction is not widely used today, but a few recent examples have been reported [7,[10][11][12][13]. One illustration is the synthesis of the anti-aromatic dehydrobenzo [12]annulene (DBA) 1 (Scheme 6-3) [12].…”

mentioning

confidence: 99%

Cross‐Coupling Reactions to sp Carbon Atoms

Marsden¹,

Haley²

2004

Metal‐Catalyzed Cross‐Coupling Reactions

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mentioning

confidence: 99%

Cross‐Coupling Reactions to sp Carbon Atoms

Marsden¹,

Haley²

2004

Metal‐Catalyzed Cross‐Coupling Reactions

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“…In the X-ray structure of 11 with longer linkers, two p-phenylene units were overlapped with a distance of 3.57 Å [43]. Six o-phenylene units form a highly twisted nonplanar structure of 12 [44]. Compounds 13 and 14 are oligomers having both o-phenylene and m-phenylene units [45].…”

Section: Benzene Macrocyclesmentioning

confidence: 98%

Three-Dimensional Aromatic Networks

Toyota

Iwanaga

2012

Topics in Current Chemistry

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Three-dimensional (3D) networks consisting of aromatic units and linkers are reviewed from various aspects. To understand principles for the construction of such compounds, we generalize the roles of building units, the synthetic approaches, and the classification of networks. As fundamental compounds, cyclophanes with large aromatic units and aromatic macrocycles with linear acetylene linkers are highlighted in terms of transannular interactions between aromatic units, conformational preference, and resolution of chiral derivatives. Polycyclic cage compounds are constructed from building units by linkages via covalent bonds, metal-coordination bonds, or hydrogen bonds. Large cage networks often include a wide range of guest species in their cavity to afford novel inclusion compounds. Topological isomers consisting of two or more macrocycles are formed by cyclization of preorganized species. Some complicated topological networks are constructed by self-assembly of simple building units.

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“…Since then, two strategies have been evolved for the assembly of 8. The first has focused on improvement of the Eglinton route by modification of the reaction conditions, either by changing the method of Cu-acetylide formation [13] or by inclusion of Pd as a catalyst [14]. The second strategy has been to develop completely new synthetic routes [16,18,20].…”

Section: Comparison Of the Two Pathwaysmentioning

confidence: 99%

“…The only ortho-PAMs in which the macrocycle contains more than twelve carbon atoms to have been prepared and characterized formally are the [16]-, [24]-, and [40]annulenes 10, 11, and 16, respectively [13,15,19]. An X-ray structure has been obtained on PAM 16 and shows that the molecule contains no symmetry other than a C 1 axis [19b].…”

Section: Agmentioning

confidence: 99%

“…PAM 8 was sublimed at 160 hC on a diffusion-pump vacuum line (10 -6 Torr) for approximately 48 h (yield 2.9 g, 48 % based on the copper acetylide). Extraction of the residue left in the sublimator with acetone, followed by column chromatography (CH 2 Cl 2 /hexanes, 1:4 elution), gave 10 (0.5 g, 8 %), together with a trace amount of 11 [13]. in THF (100 mL) and i-Pr 2 NH (100 mL) at 55 hC.…”

Section: 92mentioning

confidence: 99%

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