Molecules 2013-01-01

Photochemical synthesis and properties of 1,6- and 1,8-naphthalenophanes.

Pablo Wessig, Annika Matthes

Index: Molecules 18(1) , 1314-24, (2013)

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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 ω-(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.