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Photochemical synthesis and properties of 1,6- and 1,8-Naphthalenophanes

  • 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 omega-(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.

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Metadaten
Author:Pablo WessigORCiDGND, Annika Matthes
DOI:https://doi.org/10.3390/molecules18011314
ISSN:1420-3049 (print)
Parent Title (English):Molecules
Publisher:MDPI
Place of publication:Basel
Document Type:Article
Language:English
Year of first Publication:2013
Year of Completion:2013
Release Date:2017/03/26
Tag:atropisomerism; dynamic HPLC; dynamic NMR; naphthalenophanes; photo-dehydro-Diels-Alder reaction
Volume:18
Issue:1
Pagenumber:11
First Page:1314
Last Page:1324
Funder:Deutsche Forschungsgemeinschaft
Organizational units:Mathematisch-Naturwissenschaftliche Fakultät / Institut für Chemie
Peer Review:Referiert
Publication Way:Open Access