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A Phenyl-Ethynyl-Macrocycle: A Model Compound for "Geländer" Oligomers Comprising Reactive Conjugated Banisters
JournalArticle (Originalarbeit in einer wissenschaftlichen Zeitschrift)
 
ID 4494465
Author(s) Bannwart, Linda Maria; Jundt, Lukas; Müntener, Thomas; Neuburger, Markus; Häussinger, Daniel; Mayor, Marcel
Author(s) at UniBasel Mayor, Marcel
Bannwart, Linda Maria
Müntener, Thomas
Neuburger, Markus
Häussinger, Daniel
Year 2018
Title A Phenyl-Ethynyl-Macrocycle: A Model Compound for "Geländer" Oligomers Comprising Reactive Conjugated Banisters
Journal European Journal of Organic Chemistry
Volume 2018
Number 26
Pages / Article-Number 3391-3402
Keywords “Geländer” oligomers, Cycloaddition, Macrocycles, Chirality, Atropisomers
Abstract Macrocycle 1 is assembled as smallest member of a series of “Geländer” oligomers with a conjugated banister comprising exclusively sp2‐ and sp‐hybridized carbon atoms. The synthesis of 1 is based on an acetylene scaffolding approach, comprising Sonogashira cross‐coupling reactions in combination with protection group strategies and a final cyclization based on an oxidative acetylene coupling using Eglinton‐Breslow reaction conditions. Macrocycle 1 serves as model compound for the investigation of the structural integrity of the strained 1,3‐diyne subunit. An enhanced reactivity of the strained 1,3‐diyne subunit is documented by its engagement in Huisgen's (2+3) cycloaddition when exposed to an azide at elevated temperature. Both structures, macrocycle 1 and cycloaddition‐product 2, are fully characterized including their solid‐state structure obtained by X‐ray diffraction analysis.
Publisher WILEY-V C H VERLAG GMBH
URL https://onlinelibrary.wiley.com/doi/abs/10.1002/ejoc.201800586
edoc-URL https://edoc.unibas.ch/68436/
Full Text on edoc No
Digital Object Identifier DOI 10.1002/ejoc.201800586
ISI-Number WOS:000438718400002
Document type (ISI) Article
 
   

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