Trapping of the highly strained [5](2,4)quinolinophane system
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Publication date
2007
Authors
van Eis, M.J.
Lutz, M.
Spek, A.L.
de Wolf, W.H.
Bickelhaupt, F.
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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.
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van Eis, M J, Lutz, M, Spek, A L, de Wolf, W H & Bickelhaupt, F 2007, 'Trapping of the highly strained [5](2,4)quinolinophane system', Tetrahedron, vol. 63, pp. 1689-1694.