Molecular Ansa-Basket: Synthesis of Inherently Chiral All-Carbon [12](1,6)Pyrenophane.
Rajesh MannancherryMichael DevereuxDaniel HäussingerMarcel MayorPublished in: The Journal of organic chemistry (2019)
The synthesis of inherently chiral all-carbon C2-symmetric [12](1,6)pyrenophane 1 is reported. The cyclophane 1 was obtained via a ring-closing alkyne metathesis reaction using Mortreux's catalyst molybdenum hexacarbonyl and 2-fluorophenol as a phenol additive. The M and P enantiomers of the all-carbon pyrenophane 1 were demonstrated to be very stable in their enantiopure form even upon prolonged heating at 200 °C. [12](1,6)Pyrenophane-6-yne 1 was fully characterized by high-resolution mass spectrometry, nuclear magnetic resonance, UV-vis, and measured and calculated electronic circular dichroism spectroscopy.
Keyphrases
- magnetic resonance
- high resolution mass spectrometry
- ionic liquid
- capillary electrophoresis
- liquid chromatography
- high resolution
- room temperature
- ultra high performance liquid chromatography
- magnetic resonance imaging
- highly efficient
- computed tomography
- ms ms
- tandem mass spectrometry
- contrast enhanced
- carbon dioxide