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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

Pablo Wessig*  and Annika Matthes

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

(This article belongs to the Special Issue New Trends in Photochemistry)

Download PDF Full-Text [302 KB, uploaded 21 January 2013 10:35 CET]

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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