Phenanthro[1.10]-Annelated [3.3.3]Propellanes by Cyclodehydrogenation Reactions of Mono-, Di-, and Tribenzylidenetriptindanes

Hackfort, Thorsten; Kuck, Dietmar

doi:10.1002/(sici)1099-0690(199911)1999:11<2867::aid-ejoc2867>3.0.co;2-b

Cited by 15 publications

(3 citation statements)

References 46 publications

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“…Separation by chromatography allowed us to identify all of them by 1 H NMR spectroscopy. [26] Interestingly, the relative amounts of the four isomers were found to be very close to the statistical ratio, viz., [39] : [40] : [41] : [42] = 3 : 1 : 1 : 3. This parallels the above-mentioned finding that threefold nitration of tribenzotriquinacenes also occurs in the statistical ratio, viz., 3 : 1 in favor of the C 1symmetric isomer.…”

Section: Tetrasubstituted Centrohexaindanesmentioning

confidence: 99%

“…The propellane route involves the easily accessible triptindane-9,10,11-trione 22, which easily reacts with three equivalents of various nucleophiles including 4-methoxyphenyllithium. [28,29,42] The triol 23 was obtained as a crude product and subjected to cyclodehydration under established conditions. [10,43] The desired product of threefold cyclization, centrohexaindane 24, was isolated in very low (nonoptimized) yield (3 % from trione 22) but fully characterized (see Supporting Information).…”

Section: Selected Di-and Trisubstituted Centrohexaindanes-chiral and ...mentioning

confidence: 99%

“…So far, only one concrete attempt to construct a C 3 ‐symmetric trifunctionalized centrohexaindane of type 20 a has been accomplished (Scheme 2). The propellane route involves the easily accessible triptindane‐9,10,11‐trione 22 , which easily reacts with three equivalents of various nucleophiles including 4‐methoxyphenyllithium [28,29,42] . The triol 23 was obtained as a crude product and subjected to cyclodehydration under established conditions [10,43] .…”

Section: Selected Di‐ and Trisubstituted Centrohexaindanes–chiral And...mentioning

confidence: 99%

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A Perspective on Centrohexaindane Chemistry and a Deep‐Sleeping “Cartesian” Seed

Kuck

2024

Eur J Org Chem

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Centrohexaindane (C41H24), a structurally unique polyaromatic hydrocarbon bearing six mutually fused indane wings stretched out along the Cartesian axes of space, may be viewed as a seed for the construction of covalent and supramolecular three‐dimensional frameworks. A kaleidoscope of established and yet‐to‐be‐explored aspects of centrohexaindane chemistry is presented in this article. After addressing some ideas about the naked centrohexacyclic (and topologically nonplanar) C17‐core, which can be considered a “centrohexaquinacyne”, the diversity of known but mostly unknown functionalization patterns at the framework of centrohexaindane is addressed in increasing order of substitution at the twelve equivalent peripheral positions. The variety of centrohexaindanes bearing three identical groups is displayed including a very first access to a centrohexaindane that bears a C3‐symmetrically functionalized tribenzotriquinacene (TBTQ) unit and, thus, a potential for 3D oligocondensation. The diversity of known tetra‐ and hexasubstituted centrohexaindane derivatives is presented and conceivable synthesis strategies are discussed for even more highly functionalized derivatives. Finally, the successful access to centrohexaindanes with exhaustive functionalization and hydrocarbon extension at the twelve peripheral positions completes this overview on what may be a vastly open field, still.

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Section: Tetrasubstituted Centrohexaindanesmentioning

confidence: 99%

Section: Selected Di-and Trisubstituted Centrohexaindanes-chiral and ...mentioning

confidence: 99%

Section: Selected Di‐ and Trisubstituted Centrohexaindanes–chiral And...mentioning

confidence: 99%

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A Perspective on Centrohexaindane Chemistry and a Deep‐Sleeping “Cartesian” Seed

Kuck

2024

Eur J Org Chem

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Twist along Central C−C Bonds in a Series of Fully π‐Fused Propellanes

Kato,

Tanaka,

Okada

et al. 2024

Chemistry A European J

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Without stereogenic carbon centers, organic molecules can be chiral when they have large energy barriers for conformational inversion. In this work, conformational behaviors are investigated for a series of tricyclic propellane skeletons with increasing 6‐membered‐ring peripheral moieties fused with aromatic rings. According to theoretical calculations, trinaphtho[3.3.3]propellane has three vertical naphthalene rings like triptycene shape without torsion along the central C–C single bond. On the other hand, hexabenzo[4.4.4]propellane shows hexaphenylethane‐like ca. 60° twist along the bond with large activation energy of 64 kcal mol−1 for twist inversion because of the high congestion caused by three 6‐membered‐ring loops. Indeed, the [4.4.4]propellane gives a stable pair of chiroptical enantiomers toward heating at 146 °C. By contrast, a hybrid [4.3.3]propellane exhibits fast interconversion between two twisted conformations even at −80 °C.

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Synthesis and Electronic Properties of Triperyleno[3.3.3]Propellanes: Towards Two‐Dimensional Electronic Structures

2019

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Threefold symmetric triperyleno[3.3.3]propellanes (TPRPs), which are composed of three perylene units peri‐fused on [3.3.3]proppellane, have been synthesized and their electronic properties characterized. Unsubstituted TPRP assembles into two‐dimensional honeycomb‐like networks. TPRP displays a bathochromic‐shifted absorption band in its absorption spectrum and shows well‐separated one‐electron redox waves in a cyclic voltammogram, due to a homoconjugative interaction between perylene moieties. A radical cation species of tert‐butyl substituted TPRP shows spin delocalization over the whole of the molecule, which is derived from effective overlap of HOMOs among three perylene moieties.

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Phenanthro[1.10]-Annelated [3.3.3]Propellanes by Cyclodehydrogenation Reactions of Mono-, Di-, and Tribenzylidenetriptindanes

Cited by 15 publications

References 46 publications

A Perspective on Centrohexaindane Chemistry and a Deep‐Sleeping “Cartesian” Seed

A Perspective on Centrohexaindane Chemistry and a Deep‐Sleeping “Cartesian” Seed

Twist along Central C−C Bonds in a Series of Fully π‐Fused Propellanes

Synthesis and Electronic Properties of Triperyleno[3.3.3]Propellanes: Towards Two‐Dimensional Electronic Structures

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