Synthesis and Analysis of (γ,γ’,γ’’-Trifluoro)neopentyl (TFNP) Aryl Ethers as a Polar Fluoroaliphatic Motif
- Publication Type
- Original research
- Authors
- Fulltext
- Download
A route is developed to (γ,γ’,γ’’’-trifluoro)neopentyl (TFNP) aryl ethers to extend the methods for the introduction of the tert-butyl group, carrying a fluorine on each of the methyl substituents. The route combines neopentyltosylate 3 with phenols and thiophenols to give efficient substitution reactions to the corresponding TFNP aryl ethers. The three C−F bonds adopt a helical propeller conformation as revealed by computation and single crystal X-ray structure analysis. The LogPs of TFNP ethers are lower (more hydrophilic) than their neopentyl analogues. The metabolism of selected TFNP ethers was explored in the fungus Cunninghamella elegans.
Journal
- Title
- Chem. Eur. J. 2024, 30, e202402532 (1 of 5) © 2024
- Publisher
- whily
- Publisher Country
- United States of America
- Indexing
- Thomson Reuters
- Impact Factor
- 4.3
- Publication Type
- Both (Printed and Online)
- Volume
- 30
- Year
- 2024
- Pages
- --