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

Research output: Contribution to JournalArticleAcademicpeer-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 languageEnglish
Pages (from-to)1689-1694
JournalTetrahedron Symposia-in-Print
Volume63
DOIs
Publication statusPublished - 2007

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Alkenes
Carbon
Water
carbene

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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 Symposia-in-Print, 63, 1689-1694. https://doi.org/10.1016/j.tet.2006.11.075
van Eis, M.J. ; Lutz, M. ; Spek, A.L ; de Wolf, W.H. ; Bickelhaupt, F. / Trapping of the highly strained [5](2,4)quinolinophane system. In: Tetrahedron Symposia-in-Print. 2007 ; Vol. 63. pp. 1689-1694.
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van Eis, MJ, Lutz, M, Spek, AL, de Wolf, WH & Bickelhaupt, F 2007, 'Trapping of the highly strained [5](2,4)quinolinophane system' Tetrahedron Symposia-in-Print, vol. 63, pp. 1689-1694. https://doi.org/10.1016/j.tet.2006.11.075

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 JournalArticleAcademicpeer-review

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AU - van Eis, M.J.

AU - Lutz, M.

AU - Spek, A.L

AU - de Wolf, W.H.

AU - Bickelhaupt, F.

PY - 2007

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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

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