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Molecular Ansa-Basket: Synthesis of Inherently Chiral All-Carbon [12](1,6)Pyrenophane
Rajesh Mannancherry1, Mike Devereux1, Daniel Häussinger1
1Department of Chemistry , University of Basel , St. Johanns-Ring 19 , 4056 Basel , Switzerland.
Abstract:
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.
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