The Dibenzocyclobutadiene Dianion

Bauld, Nathan L.; Banks, D. B.

doi:10.1021/ja01079a029

Cited by 12 publications

(2 citation statements)

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“…This spin density profile in 4 •is in stark contrast with that found in the biphenylene (bi[6]annulenylene) anion radical where spin localizes on the cyclobutadienyl moiety. 8,9 These two (2 •and 4 •-) comprise the only biannulenylene anion radical systems to be reported. However, many more annulenylenes can be envisioned and presumably trapped using the technique described above.…”

Section: Resultsmentioning

confidence: 99%

Single-Electron Entrapment of [8]Annulyne, Biannulenylenes, and an Annulenoannulene

et al. 2003

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The low-temperature (-100 degrees C) dehydrohalogenation of bromocyclooctatetraene followed by immediate electron-transfer yields a stable solution of the [8]annulyne anion radical. If the unstable [8]annulyne is reacted with itself, cyclobutadiene, or benzyne, the respective bi-[8]annulenylene, [6]annuleno[8]annulene, or [6]-[8]annulenylene can be trapped as their anion radicals via one-electron transfer. These condensation products were all obtained from simple [2 + 2] cycloaddition reactions. B3LYP/6-31G geometry optimizations were carried out, and the calculated spin densities were compared to the EPR spectral results obtained for the anion radicals of [6]annuleno[8]annulene, [8]annulyne, bi[8]annulenylene, and [6]-[8]annulenylene, and excellent agreement has been realized. This simple "one-pot" approach should be applicable to a wide range of such systems.

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Section: Resultsmentioning

confidence: 99%

Single-Electron Entrapment of [8]Annulyne, Biannulenylenes, and an Annulenoannulene

et al. 2003

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“…102 In this class fall the species obtained by polarographic reduction or reduction with alkali metals in aprotic solvents, for example, benzo-COT anion radical (57)103 and its dianion (58),103 COT-cycloheptatrienyl anion (60),104 COT[6]naphthalenyl anion radical (63)103 and its dianion (64),103 and dibenzocyclobutadienyl anion radical (75). 105 Many condensed ring systems have negative TRE(PE) values. Those with TRE(PE) values in the range -0.010 to -0.040 are stable in solution at temperatures of 193 to 218 K, like benzocyclobutadienyl anion radical (42)106 and 8,9-benzobicyclo[5.2.0]nonatetraenyl anion (78).107 Some of these species, like benzocyclobutadienyl dication (41), are stable at "higher" temperatures, e.g., 240 K, in the form of a methyl derivative.…”

Section: Resultsmentioning

confidence: 99%

Topological resonance energies of conjugated ions, radicals, and ion radicals

Ilić¹,

Trinajstić²

1980

J. Org. Chem.

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Ein Quadratsäure‐bis(amidin) und ein Tetraaza‐binaphthylen: Synthese und Reaktionen

Hünig

Pütter

1977

Chem. Ber.

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Als Vertreter der bisher unbekannten Quadratsaure-bis(amidine) und ihrer Dikationen werden 5a, b bzw. 19 synthetisiert. Edukt ist das 1,3-Diamid 16, wiihrend sich das isomere 1,2-Diamid 7 und seine Derivate 8 und 10 nicht zu 5 kondensieren. 5a wird glatt zum Tetraaza-binaphthylen (Cyclobutadichinoxalin) 18, , , oxidiert, das sich reversibel reduzieren laBt unter Einschaltung des sehr stabilen Radikalanions ISse,,, (K,,, = lo''). 5 b wird zweistufig oxidiert (Kscm = 10"). Das Dikation 19 IaBt sich elektrochemisch nur irreversibel reduzieren. A Squaric Acid Bis(amidine) and a Tetraazabinaphthylene: Synthesis and Reactions') Sa, b and 19 are synthesized as examples of the hitherto unknown squaric acid bis(amidines) and their dications, respectively. Starting material is the 1Jdiamide 16, whereas the isomeric 1,Zdiamide 7 and its derivatives 8 and 10 do not yield S.5a can be smoothly oxidized to tetraazabinaphthylene (cyclobutadiquinoxaline) 18,,, which is reducible reversibly, the stable radical anion ISs., (Ks,, = being an intermediate. 5 b can be oxidized in two steps (Ks,, = 10").Electrochemical reduction of 19 is an irreversible process.

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The Dibenzocyclobutadiene Dianion

Cited by 12 publications

References 1 publication

Single-Electron Entrapment of [8]Annulyne, Biannulenylenes, and an Annulenoannulene

Single-Electron Entrapment of [8]Annulyne, Biannulenylenes, and an Annulenoannulene

Topological resonance energies of conjugated ions, radicals, and ion radicals

Ein Quadratsäure‐bis(amidin) und ein Tetraaza‐binaphthylen: Synthese und Reaktionen

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