Cross metathesis of (-)-β-pinene, (-)-limonene and terpenoids derived from limonene with internal olefins

Fernandes, Luciana Sarmento; Mandelli, Dalmo; Carvalho, Wagner A.; Caytan, Elsa; Fischmeister, Cédric; Bruneau, Christian

doi:10.1016/j.apcata.2021.118284

Applied Catalysis A: General

2021

DOI: 10.1016/j.apcata.2021.118284

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Cross metathesis of (-)-β-pinene, (-)-limonene and terpenoids derived from limonene with internal olefins

Luciana Sarmento Fernandes

Dalmo Mandelli

Wagner A. Carvalho

et al.

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Cited by 5 publications

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“…As the participation of β-pinene 31 in 1a-promoted crossmetathesis reactions is known, 26 the challenge of reaction of 31 with 3 was not unexpected. Successful cross metatheses of 31 required very large excesses of the alkene partner, excesses that were not possible with the limited availability of 3.…”

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confidence: 99%

Synthesis of trans-Tetrafluoro(trifluoromethyl)-λ⁶-sulfanyl (CF₃SF₄)-Containing Olefins via Cross Metathesis

2023

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The cross-metathesis reactions of trans-tetrafluoro(trifluoromethyl)-λ6-sulfanyl (CF3SF4)-containing olefins expand the repertoire of synthetic transformations of CF3SF4-substituted molecules. Treatment of a primary alkene and 3-CF3SF4–propene with a second-generation Hoveyda–Grubbs catalyst yielded the cross-metathesis product in good yield under very mild conditions (room temperature). CF3SF4–propene undergoes cross metathesis with substrates containing electron-withdrawing groups or electron-donating groups at room temperature or under dichloromethane reflux. The formation of the CF3SF4–propene homodimer and the utility of that dimer to undergo selective cross-metathesis reactions are described.

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confidence: 99%

Synthesis of trans-Tetrafluoro(trifluoromethyl)-λ⁶-sulfanyl (CF₃SF₄)-Containing Olefins via Cross Metathesis

2023

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Late‐stage Modification of Cage Diones by Tandem Metathesis

Kotha

Mehta

2022

Chemistry An Asian Journal

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Herein, we report the application of tandem ring‐opening cross‐metathesis (ROCM) and tandem ring‐opening cross‐metathesis followed by cross‐metathesis (ROCM/CM) in highly strained diastereomeric heptacyclic cage diones (HCCD's) catalyzed by ruthenium catalysts. These caged diastereomeric compounds have a high degree of ring strain as well as steric congestion. Therefore, the present work related to ROCM is unique and intricate as compared to simple norbornene derivatives. It is useful to prepare new hexacyclic cage derivatives suitable for high‐energy density materials. The synthetic strategy of starting cage compounds features the Diels‐Alder reaction, and [2+2] photocycloaddition as key steps.

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Nitrogen‐Containing Polymers Derived from Terpenes: Possibilities and Limitations

Scheelje

Destaso

Cramail

et al. 2022

Macro Chemistry & Physics

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Nitrogen-containing polymers are widely applied materials, including polyamides, polyurethanes, and polyureas as well as epoxy thermosets. Their indispensability and the urgent need to replace fossil-based polymers considering more sustainable alternatives lead to significant efforts in exploring renewable feedstock as potential new building blocks. Being obtained from non-edible plant parts and often occurring as waste products, terpenes represent a promising group of renewable compounds that are of possible interest in the synthesis of nitrogen-containing polymers. The structural diversity of terpenes in combination with the mechanical properties that nitrogen-containing moieties bring into polymers can give rise to novel biobased materials that outstand mechanical and thermal properties of conventional fossil-based counterparts. In this review, an overview of the use of terpene compounds in the synthesis of nitrogen-containing polymers is given, covering different approaches to make use of terpenes as a valuable pool of renewable monomers.

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Cross metathesis of (-)-β-pinene, (-)-limonene and terpenoids derived from limonene with internal olefins

Cited by 5 publications

References 39 publications

Synthesis of trans-Tetrafluoro(trifluoromethyl)-λ⁶-sulfanyl (CF₃SF₄)-Containing Olefins via Cross Metathesis

Synthesis of trans-Tetrafluoro(trifluoromethyl)-λ⁶-sulfanyl (CF₃SF₄)-Containing Olefins via Cross Metathesis

Late‐stage Modification of Cage Diones by Tandem Metathesis

Nitrogen‐Containing Polymers Derived from Terpenes: Possibilities and Limitations

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Cross metathesis of (-)-β-pinene, (-)-limonene and terpenoids derived from limonene with internal olefins

Cited by 5 publications

References 39 publications

Synthesis of trans-Tetrafluoro(trifluoromethyl)-λ6-sulfanyl (CF3SF4)-Containing Olefins via Cross Metathesis

Synthesis of trans-Tetrafluoro(trifluoromethyl)-λ6-sulfanyl (CF3SF4)-Containing Olefins via Cross Metathesis

Late‐stage Modification of Cage Diones by Tandem Metathesis

Nitrogen‐Containing Polymers Derived from Terpenes: Possibilities and Limitations

Contact Info

Product

Resources

About

Synthesis of trans-Tetrafluoro(trifluoromethyl)-λ⁶-sulfanyl (CF₃SF₄)-Containing Olefins via Cross Metathesis

Synthesis of trans-Tetrafluoro(trifluoromethyl)-λ⁶-sulfanyl (CF₃SF₄)-Containing Olefins via Cross Metathesis