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来源：百度知道 编辑：UC知道 时间：2024/06/30 09:33:58
Synthesis and Structure of Trigonal and Tetragonal Connectors
for a “Tinkertoy” Construction Set
Peter F. H. Schwab, Bruce C. Noll, and Josef Michl*
Department of Chemistry and Biochemistry, University of Colorado, Boulder, Colorado 80309-0215
michl@eefus.colorado.edu
Received February 15, 2002
We describe a convergent synthesis of eight 1,3,5- and 1,2,4,5-substituted benzene derivatives with
long rigid arms containing 4-pyridyl, 2,2¢-bipyridyl, and 2,2¢-bipyrimidyl termini, meant to be used
as trigonal or tetragonal connectors for the construction of large molecular structures. The synthesis
involved copper-free Pd-mediated coupling of terminal acetylenes to aryl halides. First, one of the
termini of 1,3-diethynylbicyclo[1.1.1]pentane was coupled with a brominated aza heterocycle, and
second, 3 equiv of the resulting extended arm were coupled with 1,3,5-triiodobenzene or 4 with
1,2,4,5-tetraiodobenzene. An improved
for a “Tinkertoy” Construction Set
Peter F. H. Schwab, Bruce C. Noll, and Josef Michl*
Department of Chemistry and Biochemistry, University of Colorado, Boulder, Colorado 80309-0215
michl@eefus.colorado.edu
Received February 15, 2002
We describe a convergent synthesis of eight 1,3,5- and 1,2,4,5-substituted benzene derivatives with
long rigid arms containing 4-pyridyl, 2,2¢-bipyridyl, and 2,2¢-bipyrimidyl termini, meant to be used
as trigonal or tetragonal connectors for the construction of large molecular structures. The synthesis
involved copper-free Pd-mediated coupling of terminal acetylenes to aryl halides. First, one of the
termini of 1,3-diethynylbicyclo[1.1.1]pentane was coupled with a brominated aza heterocycle, and
second, 3 equiv of the resulting extended arm were coupled with 1,3,5-triiodobenzene or 4 with
1,2,4,5-tetraiodobenzene. An improved
合成和结构三角和四角连接器
一个“ Tinkertoy ”建设集
彼得跳频施瓦布，布鲁斯角诺尔和约瑟夫Michl *
化学与生物化学系，科罗拉多大学，科罗拉多州博尔德80309-0215
michl@eefus.colorado.edu
收到2002年2月15号
我们描述一个收敛合成8 1,3,5 -和1,2,4,5 -取代苯衍生物的
长期僵化的武器载4 -吡啶， 2,2 ¢ -联吡啶和2,2 ¢ - bipyrimidyl总站，是用来
作为三方或四方连接器，用于建造大型分子结构。综合
参与铜免费钯介导耦合的终端炔以卤代芳烃。首先，一个
总站的1,3 - diethynylbicyclo [ 1.1.1 ]戊烷是加上溴化杂环字，并
第二， 3相当于由此产生的延长臂被加上1,3,5 triiodobenzene或4
1,2,4,5 - tetraiodobenzene 。一种改进的大规模合成1,3 - diethynylbicyclo [ 1.1.1 ]戊烷
描述。结构的两个武器，测定了单晶X射线衍射分析。
一些长期分子杆4 -吡啶基总站，得到的副产品，以及singlecrystal
X -射线结构是报告中最短的这些。