Solvent-induced, selective rearrangement of hydrogen cubane-1,4-dicarboxylate to hydrogen cuneane-2,6-dicarboxylate

Durkó, Gábor; Jalsovszky, István

doi:10.1016/j.tet.2013.04.056

Cited by 6 publications

(2 citation statements)

References 24 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…As imilar rearrangement is observed in the presence of Li cationso rp rotons (Scheme 16 b). [155] Rhodium(I) complexes rapidlyi nsert into the carbon-carbon bond of cubanes in an oxidative addition style. The intermediate five-membered metallacycle 66 is rearranged to the more staple tricyclodiene 62 (Scheme 16 c).…”

Section: Limitations Of the Carbon Skeleton-stability And Rearrangemementioning

confidence: 99%

Nonconjugated Hydrocarbons as Rigid‐Linear Motifs: Isosteres for Material Sciences and Bioorganic and Medicinal Chemistry

Locke

Bernhard

Senge

2019

Chemistry A European J

197

143

View full text Add to dashboard Cite

Nonconjugated hydrocarbons, like bicyclo[1.1.1]pentane, bicyclo[2.2.2]octane, triptycene, and cubane are a unique class of rigid linkers. Due to their similarity in size and shape they are useful mimics of classic benzene moieties in drugs, so‐called bioisosteres. Moreover, they also fulfill an important role in material sciences as linear linkers, in order to arrange various functionalities in a defined spatial manner. In this Review article, recent developments and usages of these special, rectilinear systems are discussed. Furthermore, we focus on covalently linked, nonconjugated linear arrangements and discuss the physical and chemical properties and differences of individual linkers, as well as their application in material and medicinal sciences.

show abstract

Section: Limitations Of the Carbon Skeleton-stability And Rearrangemementioning

confidence: 99%

Nonconjugated Hydrocarbons as Rigid‐Linear Motifs: Isosteres for Material Sciences and Bioorganic and Medicinal Chemistry

Locke

Bernhard

Senge

2019

Chemistry A European J

197

143

View full text Add to dashboard Cite

show abstract

“…It has also been shown that rearrangement of cubane ( 1 ) to cuneane ( 136 ) can be initialized by Li(I) with a weakly coordinating carborane anion . Computational and experimental work has since shown that similar skeletal rearrangements can be initialized to generate various derivatives or isomers of cuneane through employment of either derivatives of cubane ( 1 ) in the above conditions and/or through employment of a proton source (H + ). ,, …”

Section: Rearrangementsmentioning

confidence: 99%