ChemInform Abstract: 6,6‐Dimethyl‐ and 6,6‐Diphenylfulvene as Cycloaddents in Reaction with Moore′s Ketene.

Pârvulescu, Luminitza; Marton, Anca; Mihai, M.; Drăghici, Constantin; Varga, Richard A.; Gheorghiu, Mihaela

doi:10.1002/chin.201046053

Cited by 2 publications

(2 citation statements)

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“…Although the stereochemistry of DACs can usually be predicted by the ‘endo rule’ [92,176,229,232], there are some exceptions, particularly when sterically-demanding fulvenes, such as norbornyl-fused fulvenes [229] or adamantilydenefulvene [174] are involved. In the literature, many cycloaddition reactions have been conducted with dimethylfulvene [52,97,106,118,133–134] or diphenylfulvene [20,103,114,133,163,180]. In each instance, the endo stereochemistry of the cycloadduct is dominant [91,176,180], indicating that the fulvene substituents in the exocyclic C6 position are too distal to impact the stereoselectivity [76,229].…”

Section: Reviewmentioning

confidence: 99%

An overview of the cycloaddition chemistry of fulvenes and emerging applications

Swan¹,

Platts²,

Blencowe³

2019

Beilstein J. Org. Chem.

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The unusual electronic properties and unique reactivity of fulvenes have interested researchers for over a century. The propensity to form dipolar structures at relatively low temperatures and to participate as various components in cycloaddition reactions, often highly selectively, makes them ideal for the synthesis of complex polycyclic carbon scaffolds. As a result, fulvene cycloaddition chemistry has been employed extensively for the synthesis of natural products. More recently, fulvene cycloaddition chemistry has also found application to other areas including materials chemistry and dynamic combinatorial chemistry. This highlight article discusses the unusual properties of fulvenes and their varied cycloaddition chemistry, focussing on applications in organic and natural synthesis, dynamic combinatorial chemistry and materials chemistry, including dynamers, hydrogels and charge transfer complexes. Tables providing comprehensive directories of fulvene cycloaddition chemistry are provided, including fulvene intramolecular and intermolecular cycloadditions complete with reactant partners and their resulting cyclic adducts, which provide a useful reference source for synthetic chemists working with fulvenes and complex polycyclic scaffolds.

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Section: Reviewmentioning

confidence: 99%

An overview of the cycloaddition chemistry of fulvenes and emerging applications

Swan¹,

Platts²,

Blencowe³

2019

Beilstein J. Org. Chem.

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“…Fulvenes are a class of highly reactive intermediates , with unusual electronic properties and two main applications, the creation of complex polycyclic frameworks through cycloaddition reactions − and the synthesis of substituted cyclopentadienyl derivatives via nucleophilic addition. ,− Despite the current interest in these reactions, little has changed in fulvene synthesis methods since Thiele first prepared them in 1900 via condensation of cyclopentadiene and an aldehyde or ketone in the presence of sodium ethanolate (Scheme ). A multistep synthesis was developed by Hafner in 1964, specifically targeting highly electrophilic aldehydes and even enabling the synthesis of the unsubstituted fulvene .…”

Section: Introductionmentioning

confidence: 99%

Kinetics and Mechanism of Pyrrolidine Buffer-Catalyzed Fulvene Formation

et al. 2018

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Rapid synthesis of fulvenes is achieved using pyrrolidinium/pyrrolidine buffers in anhydrous acetonitrile. Time-dependent UV−vis absorption and NMR spectroscopy reveal that the rate and yield of fulvene formation depend strongly on both the presence of acid in the medium and the choice of solvent, and they are negatively affected by water. Kinetic data have been collected for various substrates, and the synthetic benefits of the adjusted reaction conditions are showcased. Enhancements of reaction rates are found in comparison to literature procedures. α-Unsaturated fulvenes that were previously difficult to access can now be obtained in good yields.

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ChemInform Abstract: 6,6‐Dimethyl‐ and 6,6‐Diphenylfulvene as Cycloaddents in Reaction with Moore′s Ketene.

Cited by 2 publications

References 1 publication

An overview of the cycloaddition chemistry of fulvenes and emerging applications

An overview of the cycloaddition chemistry of fulvenes and emerging applications

Kinetics and Mechanism of Pyrrolidine Buffer-Catalyzed Fulvene Formation

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