Ring‐Expansion Reactions of the Biomass Derivative Cyrene via Enamine Dihalocyclopropanation
Abstract: A ring‐expansion process for the biomass derivative Cyrene obtained from levoglucosenone has been developed using gem‐dihalocyclopropanes as intermediates. The process involves conversion of Cyrene to an enamine, reaction with an in situ generated dihalocarbene, and then ring‐opening. Competition between endocyclic and exocyclic olefinic products was switchable using solvent and temperature, and ring‐expanded alkenyl halides were obtained in 50–64 % yield from Cyrene. Under extended heating, dehalogenation occurred giving homologated levoglucosenone in 25 % overall yield from Cyrene in 3 steps.
- Location
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Deutsche Nationalbibliothek Frankfurt am Main
- Extent
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Online-Ressource
- Language
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Englisch
- Bibliographic citation
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Ring‐Expansion Reactions of the Biomass Derivative Cyrene via Enamine Dihalocyclopropanation ; day:22 ; month:02 ; year:2024 ; extent:6
European journal of organic chemistry ; (22.02.2024) (gesamt 6)
- Creator
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Puschnig, Johannes
Greatrex, Ben W.
- DOI
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10.1002/ejoc.202400031
- URN
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urn:nbn:de:101:1-2024022314211046614935
- Rights
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Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
- Last update
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14.08.2025, 10:54 AM CEST
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Associated
- Puschnig, Johannes
- Greatrex, Ben W.
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Characterization and Application of Cyrene as a Biomass‐Based Solvent for Homogeneous Heck‐Coupling Reaction
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One-loop matching and running with covariant derivative expansion
Application of hydrothermal reactions to biomass conversion
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Divergent Cascade Ring‐Expansion Reactions of Acryloyl Imides
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Chapter X Cyrene
Ægyptvs et Cyrene
XLV. Simon von Cyrene
(Bischof Laurentius zu Cyrene)
XLV. Simon von Cyrene
Characterization and Application of Cyrene as a Biomass‐Based Solvent for Homogeneous Heck‐Coupling Reaction
Polymer Chemistry Applications of Cyrene and its Derivative Cygnet 0.0 as Safer Replacements for Polar Aprotic Solvents
One-loop matching and running with covariant derivative expansion
Application of hydrothermal reactions to biomass conversion
The slow expansion with nonminimal derivative coupling and its conformal dual
Divergent Cascade Ring‐Expansion Reactions of Acryloyl Imides