Helical (5Z, 11E)dibenzo[a,e]cyclooctatetrene:: A spring-loaded monomer

被引:22
作者
Carnes, Matthew
Buccella, Daniela
Decatur, John
Steigerwald, Michael L.
Nuckolls, Colin [1 ]
机构
[1] Columbia Univ, Dept Chem, New York, NY 10027 USA
关键词
catalysis; nanotechnology; olefin metathesis; polycycles; polymers;
D O I
10.1002/anie.200704355
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Figure Presented) ROMP with a kinky olefin: An [8]-annulene in which one of the double bonds is kinked into a trans configuration is wound into a helical conformation, and is spring-loaded with circa 18 kcal mol-1 strain energy. This annulene acts as an active monomer for ring-opening polymerization (ROMP), which produces a living oligo-(phenylene vinylene) (OPV) with all-ortho linkages. The polymer has an equal number of cis and trans double bonds. © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:2982 / 2985
页数:4
相关论文
共 37 条
[1]   PHOTOCHEMICAL AND THERMAL DE-NITROGENATIONS OF AZOALKANES AS MECHANISTIC PROBES FOR THE DIRADICAL INTERMEDIATES INVOLVED IN THE DI-PI-METHANE REARRANGEMENT OF DIBENZOBARRELENE [J].
ADAM, W ;
DELUCCHI, O ;
PETERS, K ;
PETERS, EM ;
VONSCHNERING, HG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (21) :5747-5753
[2]  
BARTON JW, 1985, J CHEM SOC P1, V7, P1407
[3]  
BERENGUER MJ, 1971, TETRAHEDRON LETT, V12, P495
[4]   CONDENSED CYCLOBUTANE AROMATIC COMPOUNDS .23. SOME TRANSFORMATION PRODUCTS OF 1,2,5,6-DIBENZOCYCLO-OCTATETRAENE [J].
CAVA, MP ;
ROSE, JC ;
POHLKE, R ;
FRAENKEL, G ;
ERICKSON, BW .
TETRAHEDRON, 1962, 18 (SEP) :1005-&
[5]  
Chaffins S, 2002, SYNTHESIS-STUTTGART, P1191
[6]   MOLECULAR ASYMMETRY OF OLEFINS .1. RESOLUTION OF TRANS-CYCLOOCTENE [J].
COPE, AC ;
WINKLER, HJS ;
JOHNSON, HW ;
VANAUKEN, TV ;
GANELLIN, CR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1963, 85 (20) :3276-&
[7]   CYCLIC POLYOLEFINS .14. 3,7-DIBROMO-1,2,5,6-DIBENZCYCLOOCTADIENE AND 1,2,5,6-DIBENZCYCLOOCTATETRAENE [J].
COPE, AC ;
FENTON, SW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1951, 73 (04) :1668-1673
[8]  
CUTSHALL TW, 1972, CAN J CHEMISTRY, V50, P2364, DOI 10.1139/v72-375
[9]  
FARENHORST R, 1966, TETRAHEDRON LETT, V7, P6465
[10]   1,2,5,6-DIBENZCYCLOOCTATETRAENE [J].
FIESER, LF ;
PECHET, MM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1946, 68 (12) :2577-2580