Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2015, Issue 19, Pages 4071-4076Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201500565
Keywords
Synthetic methods; Fluorine; Organofluorine compounds; Organosilicon compounds; Cyclopropanes; Carbocations
Categories
Funding
- National Science Foundation (NSF) (CAREER) [CHE-0847262]
- Stonehill College
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [0847262] Funding Source: National Science Foundation
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A simple, high yielding, two-step, one-pot protocol for the preparation of trifluoromethyl-substituted vinylcyclopropanes from -CF3 homoallyl alcohols is disclosed. Destabilization of the cationic intermediate by the electron-withdrawing CF3 group greatly enhances neighboring group participation of the alkene, allowing ring closure to predominate. The reaction can be extended to the difluoromethyl and pentafluoroethyl group, enabling the preparation of a diverse array of fluoroalkyl-substituted vinylcyclopropanes.
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