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

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

Dept of Chemistry

extern

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]C2 bond of 2b is proposed to explain the formation of the strained ‘anti-Bredt’ type olefin 11.

Original language	Undefined/Unknown
Pages (from-to)	1689-1694
Number of pages	6
Journal	Tetrahedron
Volume	63
Publication status	Published - 2007

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Cite this

@article{5060e77424544139a80ddcbbf049d3df,

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]C2 bond of 2b is proposed to explain the formation of the strained {\textquoteleft}anti-Bredt{\textquoteright} type olefin 11.",

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

year = "2007",

language = "Undefined/Unknown",

volume = "63",

pages = "1689--1694",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Ltd",

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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]C2 bond of 2b is proposed to explain the formation of the strained ‘anti-Bredt’ type olefin 11.

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]C2 bond of 2b is proposed to explain the formation of the strained ‘anti-Bredt’ type olefin 11.

M3 - Article

SN - 0040-4020

VL - 63

SP - 1689

EP - 1694

JO - Tetrahedron

JF - Tetrahedron

ER -