A New Oxocarbon C<sub>12</sub>O<sub>6</sub> via Highly Strained Benzyne Intermediates

Butenschön, Holger

doi:10.1002/anie.200700926

Angew Chem Int Ed

2007

DOI: 10.1002/anie.200700926

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A New Oxocarbon C₁₂O₆ via Highly Strained Benzyne Intermediates

Holger Butenschön

Abstract: Some fine arynes: Elimination of triflate followed by [2+2] cycloaddition with ketene silyl acetals facilitates the formation of highly strained benzynes with one or two annulated cyclobutane rings. A prominent example based on this chemistry is the synthesis of the novel oxocarbon C12O6 (see structure).

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Cited by 11 publications

References 25 publications

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Recent Advances in Benzocyclobutene Chemistry

Kotha

Lahiri²,

Tangella

2021

Asian J Org Chem

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The benzocyclobutene (BCB) moiety is present in several bioactive natural products and medicinally interesting molecules. BCB is also a valuable synthon for building a variety of polymers by the virtue of its propensity to undergo polymerization. The research on BCB chemistry has grown in the last few decades due to its unique applications in various fields of science. In this review, we have included various methods for the preparation of BCBs and highlighted their applications in the construction of diverse complex structural frameworks. We believe that this review will be useful to synthetic chemists and polymer scientists, and we anticipate several new applications will emerge in this promising area.Scheme 1. Dihalocarbene insertion to substituted benzocyclopropenes.

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Recent Advances in Benzocyclobutene Chemistry

Kotha

Lahiri²,

Tangella

2021

Asian J Org Chem

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Bindungsbildung unter Erhalt der zweifachen Ladung: Erzeugung von C₂O₃²⁺ aus CO₂²⁺ und CO₂

et al. 2007

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Vor einhundert Jahren berichtete Berthelot über die mögliche Existenz des Kohlenoxids C 2 O 3 , Oxirandion, als cyclisches Anhydrid der Oxalsäure. [1,2] In Substanz konnte C 2 O 3 jedoch bisher nicht isoliert werden, und einer thermodynamischen Analyse von Perk und Liebman zufolge ist Oxirandion ca. 230 kJ mol À1 instabiler als die getrennten Fragmente CO + CO 2 .[3] Dieser Wert stimmt mit einer berechnteten Exothermie von 222 kJ mol À1 für den Zerfall von cyclischem C 2 O 3 in CO + CO 2 gut überein, die Peppe et al. [4] bei Versuchen zur Erzeugung von neutralem C 2 O 3 aus geeigneten ionischen Vorstufen mithilfe der Neutralisations-Reionisations-Massenspektrometrie [5] ermittelten. Zusätzlich zu dem schwach gebundenen ] ist auch die Trioxapropellan-Struktur von C 2 O 3 in einer Reihe theoretischer Arbeiten betrachtet worden. [6][7][8] Ferner wurden die einfach geladenen Ionen C 2 O 3 À und C 2 O 3 + experimentell und theoretisch untersucht; [4,9,10] dem Kation C 2 O 3 + wurde auch eine Beteiligung an Isotopenaustauschprozessen in der Erdatmosphäre zugeschrieben.[10] In der bisher einzigen theoretischen Arbeit [11]

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Bond Formation with Maintenance of Twofold Charge: Generation of C₂O₃²⁺ in the Reaction of CO₂²⁺ with CO₂

et al. 2007

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A New Oxocarbon C₁₂O₆ via Highly Strained Benzyne Intermediates

Cited by 11 publications

References 25 publications

Recent Advances in Benzocyclobutene Chemistry

Recent Advances in Benzocyclobutene Chemistry

Bindungsbildung unter Erhalt der zweifachen Ladung: Erzeugung von C₂O₃²⁺ aus CO₂²⁺ und CO₂

Bond Formation with Maintenance of Twofold Charge: Generation of C₂O₃²⁺ in the Reaction of CO₂²⁺ with CO₂

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A New Oxocarbon C12O6 via Highly Strained Benzyne Intermediates

Cited by 11 publications

References 25 publications

Recent Advances in Benzocyclobutene Chemistry

Recent Advances in Benzocyclobutene Chemistry

Bindungsbildung unter Erhalt der zweifachen Ladung: Erzeugung von C2O32+ aus CO22+ und CO2

Bond Formation with Maintenance of Twofold Charge: Generation of C2O32+ in the Reaction of CO22+ with CO2

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A New Oxocarbon C₁₂O₆ via Highly Strained Benzyne Intermediates

Bindungsbildung unter Erhalt der zweifachen Ladung: Erzeugung von C₂O₃²⁺ aus CO₂²⁺ und CO₂

Bond Formation with Maintenance of Twofold Charge: Generation of C₂O₃²⁺ in the Reaction of CO₂²⁺ with CO₂