The planar dehydro[8]annulenes

Huang, Nai Zheng; Sondheimer, Franz

doi:10.1021/ar00076a001

Cited by 50 publications

(13 citation statements)

References 57 publications

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“…In the initial synthetic study to realize planar [8]annulene, triple bonds were introduced and dibenzocyclooctadiene-3,7-diyne (1) and dibenzocyclooctatriene-7-yne (2) (Figure 4) were prepared [53][54][55]. X-ray studies of diyne 1 demonstrated that the [8]annulene core has a planar structure [56].…”

Section: Attempted Synthesesmentioning

confidence: 99%

Recent Studies on the Aromaticity and Antiaromaticity of Planar Cyclooctatetraene

2010

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Cyclooctatetraene (COT), the first 4nπ-electron system to be studied, adopts an inherently nonplanar tub-shaped geometry of D 2d symmetry with alternating single and double bonds, and hence behaves as a nonaromatic polyene rather than an antiaromatic compound. Recently, however, considerable 8π-antiaromatic paratropicity has been shown to be generated in planar COT rings even with the bond alternated D 4h structure. In this review, we highlight recent theoretical and experimental studies on the antiaromaticity of hypothetical and actual planar COT. In addition, theoretically predicted triplet aromaticity and stacked aromaticity of planar COT are also briefly described.

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Section: Attempted Synthesesmentioning

confidence: 99%

Recent Studies on the Aromaticity and Antiaromaticity of Planar Cyclooctatetraene

2010

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“…Unfortunately, only a mixture of tert-butoxy-substituted cyclooctatetraenes was obtained. [11] Much later, the capture of 14 was carried out by using the same dehydrohalogenation method. As a result, a rapid polymerization took place and the product was found to be in the form of 15 ( Figure 2).…”

Section: Planar Dehydro[8]annulenesmentioning

confidence: 99%

Our Expedition in Eight‐Membered Ring Compounds: From Planar Dehydrocyclooctenes to Tub‐Shaped Chiral Tetraphenylenes

Han

Wong

2014

The Chemical Record

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“…1) can also be called tetrabenzocyclooctatetraene or tetrabenzo [8]annulene. Being a member of the polycyclic aromatic group of compounds, initial studies of 1 were centered around exploration of the planarization of cyclooctatetraene (COT) [1]. In more recent years, a tetrabenzo-derivative of COT has been investigated thoroughly due to its interesting chemical properties and theoretical relevance to the discussion of its aromaticity.…”

Section: Introductionmentioning

confidence: 99%