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Trapping of the highly strained [5](2,4)quinolinophane system |
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| Authors: | Maurice J. van Eis Martin Lutz Willem H. de Wolf |
| Affiliation: | a Novartis Institutes for BioMedical Research, Lichtstrasse 35, CH-4056 Basel, Switzerland b Bijvoet Center for Biomolecular Research, Department of Crystal and Structural Chemistry, Utrecht University, Padualaan 8, NL-3584 CH Utrecht, The Netherlands c Scheikundig Laboratorium, Vrije Universiteit, De Boelelaan 1083, NL-1081 HV Amsterdam, The Netherlands |
| Abstract: | The highly strained [5](2,4)quinolinophane system can be generated as an intermediate (2b), which is extremely susceptible towards the attack of both nucleophilic and electrophilic species. Addition of water at the carbon bridgehead C2 occurs rapidly and is followed by rearrangements to give a strain free product 10. An unusual carbene addition at the N1 C2 bond of 2b is proposed to explain the formation of the strained ‘anti-Bredt’ type olefin 11. |
| Keywords: | Cyclophanes Strain Small rings Aromaticity |
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