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.

Orthogonal synthesis of fluorinated acridones and acridines from perfluorobenzophenone / P. Del Buttero, R. Gironda, M. Moret, A. Papagni, M. Parravicini, S. Rizzato, L. Miozzo. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1434-193X. - 2011:12(2011), pp. 2265-2271. [10.1002/ejoc.201001647]

Orthogonal synthesis of fluorinated acridones and acridines from perfluorobenzophenone

P. Del Buttero
Primo
;
S. Rizzato
Penultimo
;
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.
Fluorine; Nitrogen heterocycles; Nucleophilic substitution; Pericyclic reactions; Solvent effects
Settore CHIM/03 - Chimica Generale e Inorganica
Settore CHIM/06 - Chimica Organica
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/2434/191843
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