Abstract
| Original language | English |
|---|---|
| Pages (from-to) | 1689-1694 |
| Journal | Tetrahedron Symposia-in-Print |
| Volume | 63 |
| DOIs | |
| Publication status | Published - 2007 |
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Trapping of the highly strained [5](2,4)quinolinophane system. / van Eis, M.J.; Lutz, M.; Spek, A.L; de Wolf, W.H.; Bickelhaupt, F.
In: Tetrahedron Symposia-in-Print, Vol. 63, 2007, p. 1689-1694.Research output: Contribution to Journal › Article › Academic › peer-review
TY - JOUR
T1 - Trapping of the highly strained [5](2,4)quinolinophane system
AU - van Eis, M.J.
AU - Lutz, M.
AU - Spek, A.L
AU - de Wolf, W.H.
AU - Bickelhaupt, F.
PY - 2007
Y1 - 2007
N2 - 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.
AB - 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.
U2 - 10.1016/j.tet.2006.11.075
DO - 10.1016/j.tet.2006.11.075
M3 - Article
VL - 63
SP - 1689
EP - 1694
JO - Tetrahedron Symposia-in-Print
JF - Tetrahedron Symposia-in-Print
SN - 0040-4020
ER -