3-Heteroquadricyclanes in organic synthesis

Tochtermann, W.; Olsson, Gustaf D.

doi:10.1021/cr00095a014

Cited by 34 publications

(13 citation statements)

References 29 publications

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“…The latter obviously is less stable than its valence tautomer 17, in the literature there are numerous examples for one valence tautomer being clearly favoured. [10] The structural assignment of the arene oxide was more difficult; in solution the species was stable for a long time, but it rearranged on all efforts to isolate it. Finally, besides precipitation at low temperatures (no single crystals were obtained), we succeeded in trapping it by a hetero-Diels-Alder reaction, which furnished the epoxide 21 and thus confirmed the structure suggested for 16 (Scheme 7).…”

Section: Resultsmentioning

confidence: 99%

Gold Catalysis: Oxepines from γ‐Alkynylfurans

et al. 2007

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A ketal group in a furyl position affords arene oxides from g-alkynylfurans even with the simple goldA C H T U N G T R E N N U N G (III) chloride (AuCl 3 ) catalyst. These can either undergo Diels-Alder reactions, isomerise to stable oxepines by an oxygen-walk reaction or by the addition of water selectively be converted to phenols which differ in the position of the hydroxy group from the normal phenols formed in the gold-catalysed phenol synthesis. With a phenyl substituent on the furan, the 2-hydroxymethylpyridinato-goldA C H T U N G T R E N N U N G (III) complex, not the usual arene oxide but an oxepine is obtained, still the arene oxide can be trapped from the valence-tautomeric equilibrium by a Diels-Alder reaction.

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Section: Resultsmentioning

confidence: 99%

Gold Catalysis: Oxepines from γ‐Alkynylfurans

et al. 2007

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“…The rate of the reaction was sensitive to the linker length. The pentacyclic oxahemiquadricyclane lactones produced in this method were found to be quite stable, unlike related and more strained oxaquadricyclanes …”

Section: Cycloaddition Reactions Of Norbornadienes With Alkynesmentioning

confidence: 99%

Versatile Catalytic Reactions of Norbornadiene Derivatives with Alkynes

2020

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“…Two reviews by Wiberg [67] and by Liebman and Greenberg [68] deal with strained organic molecules with carbon skeletons. Another two contributions cover small-ring heterocycles by Murray [69] and by Tochtermann and Olsson [70], respectively. Alder's review discusses the strain effects on amine basicities [71].…”

Section: Diatomic Molecules and Polymer Chainsmentioning

confidence: 99%

Molecular Mechanochemistry: Engineering and Implications of Inherently Strained Architectures

Sheiko

2015

Topics in Current Chemistry

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Mechanical activation of chemical bonds is usually achieved by applying external forces. However, nearly all molecules exhibit inherent strain of their chemical bonds and angles as a result of constraints imposed by covalent bonding and interactions with the surrounding environment. Particularly strong deformation of bonds and angles is observed in hyperbranched macromolecules caused by steric repulsion of densely grafted polymer branches. In addition to the tension amplification, macromolecular architecture allows for accurate control of strain distribution, which enables focusing of the internal mechanical tension to specific chemical bonds and angles. As such, chemically identical bonds in self-strained macromolecules become physically distinct because the difference in bond tension leads to the corresponding difference in the electronic structure and chemical reactivity of individual bonds within the same macromolecule. In this review, we outline different approaches to the design of strained macromolecules along with physical principles of tension management, including generation, amplification, and focusing of mechanical tension at specific chemical bonds.

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3-Heteroquadricyclanes in organic synthesis

Cited by 34 publications

References 29 publications

Gold Catalysis: Oxepines from γ‐Alkynylfurans

Gold Catalysis: Oxepines from γ‐Alkynylfurans

Versatile Catalytic Reactions of Norbornadiene Derivatives with Alkynes

Molecular Mechanochemistry: Engineering and Implications of Inherently Strained Architectures

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