Trapping of the highly strained [5](2,4)quinolinophane system

M.J. van Eis; M. Lutz; A.L Spek; W.H. de Wolf; F. Bickelhaupt

doi:10.1016/j.tet.2006.11.075

Trapping of the highly strained [5](2,4)quinolinophane system

M.J. van Eis, M. Lutz, A.L Spek, W.H. de Wolf, F. Bickelhaupt

Organic Chemistry

Research output: Contribution to Journal › Article › Academic › peer-review

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 Symposia-in-Print
Volume	63
DOIs	https://doi.org/10.1016/j.tet.2006.11.075
Publication status	Published - 2007

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title = "Trapping of the highly strained [5](2,4)quinolinophane system",

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. {\textcopyright} 2006 Elsevier Ltd. All rights reserved.",

author = "{van Eis}, M.J. and M. Lutz and A.L Spek and {de Wolf}, W.H. and F. Bickelhaupt",

year = "2007",

doi = "10.1016/j.tet.2006.11.075",

language = "English",

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pages = "1689--1694",

journal = "Tetrahedron Symposia-in-Print",

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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 -