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- Title
Ring‐Expansion Reactions of the Biomass Derivative Cyrene via Enamine Dihalocyclopropanation.
- Authors
Puschnig, Johannes; Greatrex, Ben W.
- 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.
- Subjects
BIOMASS; ENAMINES; SUSTAINABLE chemistry; DEHALOGENATION; RING-opening reactions; HEATING
- Publication
European Journal of Organic Chemistry, 2024, Vol 27, Issue 9, p1
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.202400031