Issue 1, 2011
From the journal:

Chemical Communications

The norbornene mystery revealed†‡

Stephan N. Steinmann,a   Pierre Vogel,a   Yirong Mob  and  Clémence Corminboeuf*a  

* Corresponding authors

a Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne EPFL SB ISIC, Lausanne, Switzerland
E-mail: clemence.corminboeuf@epfl.ch
Fax: (+)41 (0)21 693 97 00

b Department of Chemistry, Western Michigan University, Kalamazoo, USA

Abstract

The long-standing mystery surrounding the peculiar electronic structure of norbornene and its derivatives is revealed by the direct comparisons of their properties with those of reference analogues with localized double bonds (i.e. Lewis structures). Our block-localized wavefunction analysis coupled with the computations of NMR parameters evidently supports the manifestation of a density redistribution toward an incipient retro-Diels–Alder reaction.

Graphical abstract: The norbornene mystery revealed

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Article information

DOI
https://doi.org/10.1039/C0CC00601G
Article type
Communication
Submitted
26 Mar 2010
Accepted
14 Jun 2010
First published
24 Jun 2010

Chem. Commun., 2011,47, 227-229

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The norbornene mystery revealed

S. N. Steinmann, P. Vogel, Y. Mo and C. Corminboeuf, Chem. Commun., 2011, 47, 227 DOI: 10.1039/C0CC00601G

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