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.
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收藏
页码：4160 / 4169
页数：10
相关论文
共 75 条
[1]   Exploiting [2+2] cycloaddition chemistry: achievements with allenes [J].
Alcaide, Benito ;
Almendros, Pedro ;
Aragoncillo, Cristina .
CHEMICAL SOCIETY REVIEWS, 2010, 39 (02) :783-816
[2]   Functionalized acenes and heteroacenes for organic electronics [J].
Anthony, John E. .
CHEMICAL REVIEWS, 2006, 106 (12) :5028-5048
[3]   Unexpected Dimerization of a Bis(fluorenyl)-bis(trimethylsilyl)-diallene to a Dihydroquatercyclopentadiene, an Octacyclic C36 Fragment Corresponding to 60% of C60: Reaction of the Diallene with Fe2(CO)9 [J].
Banide, Emilie V. ;
Oulie, Pascal ;
Mueller-Bunz, Helge ;
McGlinchey, Michael J. .
ORGANOMETALLICS, 2008, 27 (21) :5657-5664
[4]   Syntheses, structures, and Dimerizations of ferrocenyl- and fluorenylideneallenes:: Push-pull multiple bonds? [J].
Banide, Emilie V. ;
Ortin, Yannick ;
Chamiot, Benedicte ;
Cassidy, Andrew ;
Niehaus, Jan ;
Moore, Angela ;
Seward, Corey M. ;
Mueller-Bunz, Helge ;
McGlinchey, Michael J. .
ORGANOMETALLICS, 2008, 27 (16) :4173-4182
[5]   From allenes to tetracenes:: A synthetic and structural study of silyl- and halo-allenes and their dimers [J].
Banide, Emilie V. ;
Molloy, Bevin C. ;
Ortin, Yannick ;
Mueller-Bunz, Helge ;
McGlinchey, Michael J. .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (16) :2611-2622
[6]   From allenes to tetracenes: Syntheses, structures, and reactivity of the intermediates [J].
Banide, Emilie V. ;
Oulie, Pascal ;
McGlinchey, Michael J. .
PURE AND APPLIED CHEMISTRY, 2009, 81 (01) :1-17
[7]   Sequential formation of yellow, red, and orange 1-phenyl-3,3-biphenylene-allene dimers prior to blue tetracene formation:: Helicity reversal in trans-3,4-diphenyl-1,2-bis(fluorenylidene)cyclobutane [J].
Banide, EV ;
Ortin, Y ;
Seward, CM ;
Harrington, LE ;
Muller-Bunz, H ;
McGlinchey, MJ .
CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (12) :3275-3286
[8]   SYNTHESIS OF 3,2'-5',3'-TERTHIOPHENE AND OTHER TERTHIOPHENES BY THE THIOPHENECARBOXALDEHYDE-]ETHYNYLTHIOPHENE-]DITHIENYLBUTADIYNE ROUTE [J].
BENY, JP ;
DHAWAN, SN ;
KAGAN, J ;
SUNDLASS, S .
JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (11) :2201-2204
[9]   High-Performance Organic Field-Effect Transistors [J].
Braga, Daniele ;
Horowitz, Gilles .
ADVANCED MATERIALS, 2009, 21 (14-15) :1473-1486
[10]   DIMERIZATION OF SUBSTITUTED 1,3-DIARYLALLENES [J].
BRATTESANI, AJ ;
MAVERICK, E ;
MUSCIO, OJ ;
JACOBS, TL .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (26) :7346-7349
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