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A Phenyl‐Ethynyl‐Macrocycle: A Model Compound for “Geländer” Oligomers Comprising Reactive Conjugated Banisters
Author(s) -
Bannwart Linda Maria,
Jundt Lukas,
Müntener Thomas,
Neuburger Markus,
Häussinger Daniel,
Mayor Marcel
Publication year - 2018
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201800586
Subject(s) - chemistry , cycloaddition , sonogashira coupling , acetylene , conjugated system , reactivity (psychology) , coupling reaction , azide , stereochemistry , polymer chemistry , photochemistry , catalysis , organic chemistry , palladium , medicine , alternative medicine , pathology , polymer
Macrocycle 1 is assembled as smallest member of a series of “Geländer” oligomers with a conjugated banister comprising exclusively sp 2 ‐ 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.