Herein 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. © 2011 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
Braga, D., Jaafari, A., Miozzo, L., Moret, M., Rizzato, S., Papagni, A., et al. (2011). The Rubrenic Synthesis: The Delicate Equilibrium between Tetracene and Cyclobutene. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011(22), 4160-4169 [10.1002/ejoc.201100033].
The Rubrenic Synthesis: The Delicate Equilibrium between Tetracene and Cyclobutene
BRAGA, DANIELE;MIOZZO, LUCIANO;MORET, MASSIMO;PAPAGNI, ANTONIO;
2011
Abstract
Herein 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. © 2011 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
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