The question of delocalization in "anchored" ions with potential trishomoaromatic character. 1. Reduction of tricyclo[5.4.1.04,12]dodeca-2,5,8,10-tetraene as a route to the 10.pi.11C dianion

Paquette, Leo A.; Kukla, Michael J.; Ley, Steven V.; Traynor, Sean G.

doi:10.1021/ja00456a037

Cited by 15 publications

(1 citation statement)

References 17 publications

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“…For 19b: NMR (CDClg) 6Me4Si 6.10-5.95 (dd, J = 6 and 2.3 Hz, 2, olefinic), 5.75-5.57 (octet, 2, olefinic), 3.92 (d with fine splitting, J = 8 Hz, bisallylic), 3.9-3.5 (m, superimposed on q, J = 7.5 Hz, 2, >CHOH and apical), 3.1-2.9 (m, 2, allylic),and 2.0 (br s, l,OH); MS caled, m/e 134.07315; MS found, m/e 134.07333. exo-cis-Dihydroindenyl Alcohol (18b). To 18a (150 mg, 0.85 mmol) in methanol (8 mL)-water (1.5 mL) was added potassium carbonate (600 mg, 4.3 mmol), and the resulting suspension was stirred under nitrogen for 3.75 h. The methanol was evaporated, and the residue was diluted with water and extracted four times with dichloromethane.…”

Section: Methodsmentioning

confidence: 99%

Stereoelectronic control of 2-nortriquinacenylamine deaminations. Relevance of geometry and proximity to long-range orbital interaction and charge stabilization in cup-shaped molecules

Berk¹,

Degenhardt²,

Paquette³

1978

J. Org. Chem.

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Section: Methodsmentioning

confidence: 99%

Stereoelectronic control of 2-nortriquinacenylamine deaminations. Relevance of geometry and proximity to long-range orbital interaction and charge stabilization in cup-shaped molecules

Berk¹,

Degenhardt²,

Paquette³

1978

J. Org. Chem.

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Die charakteristischen Eigenschaften homoaromatischer Systeme

Paquette

1978

Angew. Chem.

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Verbindungen mit homoaromatischen Eigenschaften sind nach wie vor ein auflerordentlich interessantes Gebiet der Chemie. Derzeit wird u. a. versucht, das AusmaR der weitreichenden Delokalisierung von Elektronen experimentell zu bestimmen, die Wechselwirkungen in Molekiilen mit zwei oder mehr isolierenden Atomen zu ermitteln und energetische sowie geometrische Eigenschaften der homoaromatischen Systeme theoretisch abzuschatzen. In diesem Aufsatz werden in erster Linie neuere spektroskopische und strukturelle Befunde kritisch besprochen; daneben werden die Reaktionen analysiert, die den Zugang zu homoaromatischen Ionen ermoglichen. Ausfuhrlich diskutiert werden mono-, bis-und trishomoaromatische Systeme, und zwar getrennt nach kationischen, anionischen und neutralen Spezies. Zuvor wird kurz die Orbitaliiberlappung in diesen Verbindungen dargestellt.

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The Realities of Extended Homoaromaticity

Paquette

1978

Angew. Chem. Int. Ed. Engl.

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Homoaromaticity has been the subject of many investigations and continues to remain an extraordinarily rich area of chemistry. Quantitative experimental evaluation of the level of long range delocalization and assessment of interactions in molecules having two or more insulating atoms, together with various theoretical estimates of energies and geometries, are areas currently being examined. The primary intention of this review is to provide a critical up-to-date survey of relevant spectral and structural data, as well as an analysis of the many reactions believed to involve generation of homoaromatic ions. Extensively discussed are mono-, bis-, and trishomoaromatic systems arranged on the basis of their cationic, anionic, or uncharged nature. Presentation of these individualized segments is preceded by a brief analysis of homoaromatic overlap.

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The question of delocalization in "anchored" ions with potential trishomoaromatic character. 1. Reduction of tricyclo[5.4.1.04,12]dodeca-2,5,8,10-tetraene as a route to the 10.pi.11C dianion

Cited by 15 publications

References 17 publications

Stereoelectronic control of 2-nortriquinacenylamine deaminations. Relevance of geometry and proximity to long-range orbital interaction and charge stabilization in cup-shaped molecules

Stereoelectronic control of 2-nortriquinacenylamine deaminations. Relevance of geometry and proximity to long-range orbital interaction and charge stabilization in cup-shaped molecules

Die charakteristischen Eigenschaften homoaromatischer Systeme

The Realities of Extended Homoaromaticity

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