The electrochemical and chemical reduction of some phenyl substituted cyclooctatetraenes

Rieke, Reuben D.; Copenhafer, Robert A.

doi:10.1016/s0022-0728(74)80041-0

Cited by 12 publications

(1 citation statement)

References 59 publications

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“…Comparison of this spectrum with that of neutral 3 in THF-t/g (6.49 (s, He), 6.41 (d ,J= 12 Hz, Hc), 5.92 (dd, J = 12 and 2 Hz, Hb), and 5.80 (d, J = 2 Hz, Ha)) reveals the benzenoid protons to be downfield shifted ( = -0.18 ppm) but Ha-Hc to be substantially shielded ( = +0.87, 0.99, and 0.84-1.07 ppm, respectively). These characteristics differ from those observed for benzo-COT11 (5, 6TMSTHF"ds 7.13 (dd, 2, Hf), 5 6…”

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confidence: 99%

Dicyclooctatetraeno[1,2:4,5]benzene dianion and tetraanion. Experimental assessment of extended paratropic vs. restricted diatropic .pi.-electron delocalization

Paquette¹,

Ewing²,

Traynor³

et al. 1977

J. Am. Chem. Soc.

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mentioning

confidence: 99%

Dicyclooctatetraeno[1,2:4,5]benzene dianion and tetraanion. Experimental assessment of extended paratropic vs. restricted diatropic .pi.-electron delocalization

Paquette¹,

Ewing²,

Traynor³

et al. 1977

J. Am. Chem. Soc.

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Cathodic Reactions of Hydrocarbons, Olefins, and Aromatic Compounds

Heınze

2004

Encyclopedia of Electrochemistry

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The sections in this article are Introduction Reductive Generation of Anionic Species Experimental Background Redox Properties Electron‐transfer Kinetics Chemical Reactions of Electrogenerated Anions Homogeneous Electron Transfer Electrophilic and Related Reactions Protonation Alkylation Acylation Addition of CO 2 and SO 3 Reductive Coupling Intramolecular Reactions Conformational Changes Bond‐breaking and Bond‐making Reactions

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Helically Chiral π‐Expanded Azocines Through Regioselective Beckmann Rearrangement and Their Charged States

Borstelmann,

Schneider,

Rominger

et al. 2024

Angewandte Chemie

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We report a synthetic approach to p‐expanded [6]helicenes incorporating tropone and azocine units in combination with a 5‐membered ring, which exhibit intriguing structural, electronic, and chiroptical properties. The regioselective Beckmann rearrangement allows the isolation of helical scaffolds containing 8‐membered lactam, azocine, and amine units. As shown by X‐ray crystallographic analysis, the incorporation of tropone or azocine units leads to highly distorted [6]helicene moieties, with distinct packing motifs in the solid state. The compounds exhibit promising optoelectronic properties with considerable photoluminescence quantum yields and tunable emission wavelengths depending on the relative position of the nitrogen center within the polycyclic framework. Separation of the enantiomers by chiral high‐performance liquid chromatography (HPLC) allowed characterization of their chiroptical properties by circular dichroism (CD) and circularly polarized luminescence (CPL) spectroscopy. The azocine compounds feature manifold redox chemistry, allowing for the characterization of the corresponding radical anions and cations as well as the dications and dianions, with near‐infrared (NIR) absorption bands extending beyond 3000 nm. Detailed theoretical studies provided insights into the aromaticity evolution upon reduction and oxidation, suggesting that the steric strain prevents the azocine unit from undergoing aromatization, while the indene moiety dominates the observed redox chemistry.

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The electrochemical and chemical reduction of some phenyl substituted cyclooctatetraenes

Cited by 12 publications

References 59 publications

Dicyclooctatetraeno[1,2:4,5]benzene dianion and tetraanion. Experimental assessment of extended paratropic vs. restricted diatropic .pi.-electron delocalization

Dicyclooctatetraeno[1,2:4,5]benzene dianion and tetraanion. Experimental assessment of extended paratropic vs. restricted diatropic .pi.-electron delocalization

Cathodic Reactions of Hydrocarbons, Olefins, and Aromatic Compounds

Helically Chiral π‐Expanded Azocines Through Regioselective Beckmann Rearrangement and Their Charged States

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