The synthesis of a dicyclopenta[a,e]pentalene via a molybdenum hexacarbonyl-mediated tandem allenic Pauson-Khand reaction

被引:50
作者
Cao, H
Flippen-Anderson, J
Cook, JM
机构
[1] Univ Wisconsin, Dept Chem, Milwaukee, WI 53201 USA
[2] USN, Res Lab, Struct Matter Lab, Washington, DC 20375 USA
关键词
D O I
10.1021/ja021159+
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An approach to the 14π annulene has been developed, by employing the molybdenum hexacarbonyl-mediated tandem allenic Pauson-Khand reaction as a key step. A di-triisopropylsilyl substituted dicyclopenta[a,e]pentalene was synthesized. This 14π annulene showed some electronic delocalization, which was not observed in previous cases. Copyright © 2003 American Chemical Society.
引用
收藏
页码:3230 / 3231
页数:2
相关论文
共 16 条
[1]  
BRANDSMA L, 1981, SYNTHESIS ACETYLENES, P155
[2]   An intramolecular allenic [2+2+1]cycloaddition [J].
Brummond, KM ;
Wan, HH ;
Kent, JL .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (19) :6535-6545
[3]   The molybdenum-mediated tandem Pauson-Khand reaction. High yield entry into [5.5.5.5]tetracyclic systems [J].
Cao, H ;
Van Ornum, SG ;
Cook, JM .
TETRAHEDRON LETTERS, 2000, 41 (28) :5313-5316
[4]   One-step synthesis of dialkynyl-1,2-diones and their conversion to fused pyrazines bearing enediyne units [J].
Faust, R ;
Weber, C ;
Fiandanese, V ;
Marchese, G ;
Punzi, A .
TETRAHEDRON, 1997, 53 (43) :14655-14670
[5]  
GLIDEWELL C, 1988, CHEM SCRIPTA, V28, P385
[6]   HUCKEL MOLECULAR ORBITAL PI RESONANCE ENERGIES - NONALTERNANT HYDROCARBONS [J].
HESS, BA ;
SCHAAD, LJ .
JOURNAL OF ORGANIC CHEMISTRY, 1971, 36 (22) :3418-&
[7]   MOLYBDENIUM MEDIATED PREPARATION OF CYCLOPENTENONES [J].
JEONG, N ;
LEE, SJ ;
LEE, BY ;
CHUNG, YK .
TETRAHEDRON LETTERS, 1993, 34 (25) :4027-4030
[8]   A NEW ALLENIC PAUSON-KHAND CYCLOADDITION FOR THE PREPARATION OF ALPHA-METHYLENE CYCLOPENTENONES [J].
KENT, JL ;
WAN, HH ;
BRUMMOND, KM .
TETRAHEDRON LETTERS, 1995, 36 (14) :2407-2410
[9]   STEREOSPECIFIC DEOXYGENATION OF 1,2-DIOLS TO OLEFINS [J].
KING, JL ;
POSNER, BA ;
MAK, KT ;
YANG, NCC .
TETRAHEDRON LETTERS, 1987, 28 (34) :3919-3922
[10]  
LEWIS D, 1975, FACTS THEORIES AROMA, P28