The Rubrenic Synthesis: The Delicate Equilibrium between Tetracene and Cyclobutene

被引：23

作者：

Braga, Daniele ^{[2
]}

Jaafari, Abdelhafid ^{[3
]}

Miozzo, Luciano ^{[1
,2
]}

Moret, Massimo ^{[1
]}

Rizzato, Silvia ^{[4
]}

Papagni, Antonio ^{[1
]}

Yassar, Abderrahim ^{[2
]}

机构：

[1] Univ Milano Bicocca, Dipartimento Sci Mat, I-20125 Milan, Italy

[2] Univ Paris Diderot, CNRS, ITODYS, UMR 7086, F-75205 Paris 13, France

[3] Univ Hassan 1Er, Fac Sci & Tech Settat, Settat, Morocco

[4] Univ Milan, Dipartimento Chim Strutturale & Stereochim Inorga, I-20133 Milan, Italy

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2011年 / 2011卷 / 22期

关键词：

Allenes; Arenes; Fused ring systems; Reaction mechanisms; Grignard reaction; THERMAL REARRANGEMENT; CONVENIENT SYNTHESIS; DIMERIZATION; HYDROCARBON; TEMPERATURE; STEREOCHEMISTRY; 1,5-HEXADIYNE; DERIVATIVES; REACTIVITY; TRANSPORT;

D O I：

10.1002/ejoc.201100033

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Herein we describe the synthesis of new substituted tetra-aryltetracenes, 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.

引用

页码：4160 / 4169

页数：10

共 75 条

[41] ARYL-SUBSTITUTED PROPARGYL ALCOHOLS AND RELATED COMPOUNDS [J].