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Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
Fully Bridged Triphenylamines Comprising Five- and Seven-Membered Rings
Ina Michalsky1,2, Viktoria Gensch3, Christian Walla4
1Organisch-Chemisches Institut, Universität Heidelberg, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany.
Abstract:
A family of fully bridged triphenylamines with embedded 5- and 7-membered rings is presented. The compounds are potent electron donors capable to undergo donor/acceptor interactions with strong cyano-based acceptors both in the solid state and solution. These interactions were evaluated by IR and UV/vis spectroscopy as well as X-ray crystallography. The vinylene-bridged compound was oxidized to the corresponding 1,2-diketone which readily underwent acid-catalyzed condensation with selected 1,2-phenylenediamines. The resulting π-extended quinoxaline derivatives represent valuable building blocks for the development of functional chromophores upon appropriate functionalization.
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