Synthesis, structure and some reactions of a multi-bridged unsaturated cyclooctadecane derivative formally having two cycloheptatrienes

被引：3
|
作者：
Kuroda, Shigeyasu
Hirano, Isao
Zhanga, Yanmei
Thanh, Nguyen Chung
Oda, Mitsunori
机构：
[1] Univ Toyama, Fac Engn, Dept Appl Chem, Toyama 9308555, Japan
[2] Shinshu Univ, Fac Sci, Dept Chem, Matsumoto, Nagano 3908621, Japan
来源：
TETRAHEDRON LETTERS | 2007年 / 48卷 / 33期
关键词：
cycloheptatriene-norcaradiene equilibrium; X-ray crystallographic; analysis; semi-empirical molecular orbital calculation; annulation;
D O I：
10.1016/j.tetlet.2007.06.096
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Double annulation of 1.6-bis(bromomethyl)-1,3,5-cycloheptatriene with diethyl acetonedicarboxylate under basic conditions provided the title cyclooctadecane derivative having formally two 1,3,5-cycloheptatriene moieties. An NMR study of tile compound suggested that one moiety stays as a cycloheptatriene form and the other as a norcaradiene form. X-ray crystallographic analysis revealed that two methano bridges have syn- and anti-configurations to the central carbonyl bridge and also showed that one of the moieties having the syn-methano bridge stays a CHT form and the other having the anti-methano bridge stays an NCD form. (c) 2007 Elsevier Ltd. All rights reserved.
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页码：5811 / 5815
页数：5
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