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The Rubrenic Synthesis: The Delicate Equilibrium between Tetracene and Cyclobutene

By D. Braga, A. Jaafari, L. Miozzo, M. Moret, S. Rizzato, A. Papagni and A. Yassar

Abstract

International audienceHerein we describe the synthesis of new substituted tetraaryltetracenes, obtained by the dimerization of triarylchloroallenes, prepared from propargyl alcohols. The propargyl alcohols were prepared by two different synthetic strategies and then the alcohols were treated to obtain the corresponding acenes. In addition to the expected tetracene derivatives, we observed the formation of bis(alkylidene)cyclobutenes. When strong electron-donating substituents were present, the main product was the cyclobutene. We discuss a reaction mechanism that accounts for the formation of the cyclobutenes

Topics: [ CHIM.ORGA ] Chemical Sciences/Organic chemistry, [ CHIM.MATE ] Chemical Sciences/Material chemistry
Publisher: Wiley-VCH Verlag
Year: 2011
DOI identifier: 10.1002/ejoc.201100033
OAI identifier: oai:HAL:hal-00822309v1
Provided by: Hal-Diderot
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