Polyquinanes. A Simple Synthesis of Tricyclo[5.2.1.0(4,10)]deca-2,5,8-triene.

Jacobson, Israel; Kofod, Hans; Launosalo, Tauno; Cyvín, S. J.; Hägen, G.

doi:10.3891/acta.chem.scand.21-2235

Cited by 74 publications

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“…The chemistry of the polyquinanes was described in several impressive surveys, such as Trost's[88] and Paquette's[89,90] review articles, the research towards dodecahedrane by Paquette[91] and Prinzbach[92] was highly impressive, and Greenberg and Liebman had published their inspiring book on strained organic molecules [93]. A number of groups, including Deslongchamps et al.,[94] Jacobson,[95] de Meijere et al.,[96] Cook et al [97]. and Serratosa et al [98].…”

Section: Cyclization Reactions In Solution: From Simple Indanes To Cementioning

confidence: 99%

From Fragmentation to Construction—from Void to Massive: Fascination with Organic Mass Spectrometry and the Synthesis of Novel Three‐Dimensional Polycyclic Aromatic Hydrocarbons

Kuck

2015

The Chemical Record

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Detailed insights gained from our research into the gas-phase chemistry of ionized and protonated diphenylalkanes and their congeners, obtained by extended synthesis of isotopically labeled model compounds and mass spectrometry, are presented and merged with those acquired during our development of a new family of polycyclic hydrocarbons, the centropolyindanes. Aside from a Personal Account that describes "two scientific lives in one", it is demonstrated, on the one hand, how our understanding of organic chemistry can help to shed light on the details of mass spectrometric fragmentation and to unravel, in a more fundamental way, the unimolecular reactivity of gaseous ions. On the other hand, it is shown how unexpected reactivity of related ions in solution, being subject to the very same fundamentals of organic chemistry, can lead to the construction of novel and, in part, unique three-dimensional polycyclic structures that may contribute to future research in material science. Two such apparently independent fields of organic chemistry may be seen as joint contributions of the art of science.

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Section: Cyclization Reactions In Solution: From Simple Indanes To Cementioning

confidence: 99%

From Fragmentation to Construction—from Void to Massive: Fascination with Organic Mass Spectrometry and the Synthesis of Novel Three‐Dimensional Polycyclic Aromatic Hydrocarbons

Kuck

2015

The Chemical Record

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“…The icosahedral point group possesses ten C 3 axes and six C 5 axes, and synthetic proposals have taken advantage of both types of symmetry elements. The former prompted Woodward [ 24 ] and Jacobson [ 25 ] independently from each other to suggest that two triquinacene units could be coupled ( Scheme 8 ). The requisite C 10 H 10 moiety, 44 , has been prepared (most elegantly via Paquette’s domino Diels–Alder route [ 26 ]) but all attempts at controlled dimerization (even on a transition metal template [ 27 ]) have so far proven fruitless.…”

Section: Reviewmentioning

confidence: 99%

Reciprocal polyhedra and the Euler relationship: cage hydrocarbons, C_nH_n and closo-boranes [B_xH_x]²⁻

McGlinchey

Hopf²

2011

Beilstein J. Org. Chem.

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SummaryThe closo-boranes BxHx +2, or their corresponding anions [BxHx]2− (where x = 5 through 12) and polycycloalkanes CnHn (where n represents even numbers from 6 through 20) exhibit a complementary relationship whereby the structures of the corresponding molecules, e.g., [B6H6]2− and C8H8 (cubane), are based on reciprocal polyhedra. The vertices in the closo-boranes correspond to faces in its polycyclic hydrocarbon counterpart and vice versa. The different bonding patterns in the two series are described. Several of these hydrocarbons (cubane, pentagonal dodecahedrane and the trigonal and pentagonal prismanes) are known while others still remain elusive. Synthetic routes to the currently known CnHn highly symmetrical polyhedral species are briefly summarized and potential routes to those currently unknown are discussed. Finally, the syntheses of the heavier element analogues of cubane and the prismanes are described.

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confidence: 99%

“…Triquinacene and its derivatives (Figure 1), which are concave tricyclich ydrocarbon compounds and first prepared by Woodward in 1964, are important in both structural organic chemistry and synthetic chemistry. [1] Thep ossible existence of homoaromatic stabilization in triquinacene had attracted much attention among organic and physical organic chemists in the past half century. [2,3] If one or more carbon atoms in triquinacene could be replacedb yh eteroatoms such as the Na tom, its aza-analogues (i.e, aza-triquinacene derivatives) might exhibit physicala nd chemical properties very different from those of triquinacene.…”

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confidence: 99%

Efficient Synthesis of Aza‐triquinacene Derivatives via Cycloaddition of 2,6‐Diazasemibullvalenes with Nitroso Compounds

Zhan

Zhang

Huang

et al. 2014

Chemistry An Asian Journal

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The reaction between 2,6-diazasemibullvalenes and nitroso compounds was investigated. Aza-triquinacene derivatives of interesting structural and synthetic chemistry were generated highly selectively in good to excellent isolated yields. This reaction, which was rarely found between common aziridine derivatives and nitroso compounds, could be attributed to the rigid polycyclic ring system and the substitution patterns of 2,6-diazasemibullvalenes. Δ(1) -Bipyrroline derivatives were formed in excellent yields when these aza-triquinacene derivatives were treated with SmI2 .

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Polyquinanes. A Simple Synthesis of Tricyclo[5.2.1.0(4,10)]deca-2,5,8-triene.

Cited by 74 publications

References 0 publications

From Fragmentation to Construction—from Void to Massive: Fascination with Organic Mass Spectrometry and the Synthesis of Novel Three‐Dimensional Polycyclic Aromatic Hydrocarbons

From Fragmentation to Construction—from Void to Massive: Fascination with Organic Mass Spectrometry and the Synthesis of Novel Three‐Dimensional Polycyclic Aromatic Hydrocarbons

Reciprocal polyhedra and the Euler relationship: cage hydrocarbons, C_nH_n and closo-boranes [B_xH_x]²⁻

Efficient Synthesis of Aza‐triquinacene Derivatives via Cycloaddition of 2,6‐Diazasemibullvalenes with Nitroso Compounds

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Polyquinanes. A Simple Synthesis of Tricyclo[5.2.1.0(4,10)]deca-2,5,8-triene.

Cited by 74 publications

References 0 publications

From Fragmentation to Construction—from Void to Massive: Fascination with Organic Mass Spectrometry and the Synthesis of Novel Three‐Dimensional Polycyclic Aromatic Hydrocarbons

From Fragmentation to Construction—from Void to Massive: Fascination with Organic Mass Spectrometry and the Synthesis of Novel Three‐Dimensional Polycyclic Aromatic Hydrocarbons

Reciprocal polyhedra and the Euler relationship: cage hydrocarbons, CnHn and closo-boranes [BxHx]2−

Efficient Synthesis of Aza‐triquinacene Derivatives via Cycloaddition of 2,6‐Diazasemibullvalenes with Nitroso Compounds

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Reciprocal polyhedra and the Euler relationship: cage hydrocarbons, C_nH_n and closo-boranes [B_xH_x]²⁻