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Molecules 2013, 18(1), 1314-1324; doi:10.3390/molecules18011314
Article

Photochemical Synthesis and Properties of 1,6- and 1,8-Naphthalenophanes

*  and
Institut für Chemie, Universität Potsdam, Karl-Liebknecht-Str. 24-25, D-14476 Potsdam, Germany
* Author to whom correspondence should be addressed.
Received: 20 December 2012 / Revised: 9 January 2013 / Accepted: 15 January 2013 / Published: 21 January 2013
(This article belongs to the Special Issue New Trends in Photochemistry)
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Abstract

Various 1,6- and 1,8-naphthalenophanes were synthesized by using the Photo-Dehydro-Diels-Alder (PDDA) reaction of bis-ynones. These compounds are easily accessible from w-(3-iodophenyl)carboxylic acids in three steps. The obtained naphthalenophanes are axially chiral and the activation barrier for the atropisomerization could be determined in some cases by means of dynamic NMR (DNMR) and/or dynamic HPLC (DHPLC) experiments.
Keywords: photo-dehydro-Diels-Alder reaction; naphthalenophanes; atropisomerism; dynamic NMR; dynamic HPLC photo-dehydro-Diels-Alder reaction; naphthalenophanes; atropisomerism; dynamic NMR; dynamic HPLC
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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Wessig, P.; Matthes, A. Photochemical Synthesis and Properties of 1,6- and 1,8-Naphthalenophanes. Molecules 2013, 18, 1314-1324.

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