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{double bond, long}C2 bond of 2b is proposed to explain the formation of the strained 'anti-Bredt' type olefin 11. © 2006 Elsevier Ltd. All rights reserved.
| Original language | English |
|---|---|
| Pages (from-to) | 1689-1694 |
| Journal | Tetrahedron |
| Volume | 63 |
| DOIs | |
| Publication status | Published - 2007 |
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CCDC 605984: Experimental Crystal Structure Determination
Van Eis, M. J. (Contributor), Lutz, M. (Contributor), Spek, A. L. (Contributor), De Wolf, W. H. (Contributor) & Bickelhaupt, F. (Contributor), Unknown, 1 Jan 2007
DOI: 10.5517/ccnbkwd, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccnbkwd&sid=DataCite
Dataset / Software: Dataset
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CCDC 261574: Experimental Crystal Structure Determination
Van Eis, M. J. (Contributor), Lutz, M. (Contributor), Spek, A. L. (Contributor), De Wolf, W. H. (Contributor) & Bickelhaupt, F. (Contributor), Unknown, 1 Jan 2007
DOI: 10.5517/cc8s5w2, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc8s5w2&sid=DataCite
Dataset / Software: Dataset