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Photochemical Synthesis and Properties of 1,6- and 1,8-Naphthalenophanes
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; in revised form: 9 January 2013 / Accepted: 15 January 2013 / Published: 21 January 2013
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
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Wessig, P.; Matthes, A. Photochemical Synthesis and Properties of 1,6- and 1,8-Naphthalenophanes. Molecules 2013, 18, 1314-1324.
Wessig P, Matthes A. Photochemical Synthesis and Properties of 1,6- and 1,8-Naphthalenophanes. Molecules. 2013; 18(1):1314-1324.
Wessig, Pablo; Matthes, Annika. 2013. "Photochemical Synthesis and Properties of 1,6- and 1,8-Naphthalenophanes." Molecules 18, no. 1: 1314-1324.