Question

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Attachment of Three Arms to a Benzene Ring.
Attempts to use the same reaction conditions for the
coupling of the remaining terminal acetylene unit of the
resulting rod 15 to 1,3,5-triiodobenzene15 in triethylamine
were initially unsuccessful. The intermediates and products
were insoluble, and the reaction did not go to
completion. The use of piperidine solved the problem.
When the temperature was kept under 55 °C to avoid
reductive removal of the C-I bonds and the degradation
of the arms, 1,3,5-tris((3-(2,2¢-bipyrimidin-5-yl)ethynyl)-
bicyclo[1.1.1]pent-1-ylethynyl)benzene (1) was formed in
about 70% yield (Scheme 3). It is best to use 15 in a 5%
excess in order to compensate for a small loss of material
due to oxidative ethyne homocoupling. The stepwise
progress of the reaction was followed by 1H NMR. The
trigonal connector 1 is chemically and thermally stable
but suffers from very low solubility in hexanes, benzene,
toluene, ethers, alcohols, ethyl acetate, and acetonitrile;
it only dissolves well in chloroform and methylene
chloride and moderately well in DMF. The coupling of
20-23 (Scheme 3) to 1,3,5-triiodobenzene proceeded
similarly.

Answer 1

扣押了三个苯环。
尝试使用相同的反应条件
耦合其余终端乙炔股
造成15杆，以1,3,5 triiodobenzene15在三乙胺
最初是不成功的。中间体及产品
为不溶性，反应没有去
完成。使用哌解决了这个问题。
当温度下保持55 ℃ ，以避免
还原去除氯债券和退化
武器， 1,3,5三（ （ 3 - （ 2,2 ¢ - bipyrimidin - 5 -基）乙炔） -
双环[ 1.1.1 ]压抑- 1 - ylethynyl ）苯（ 1 ）成立于
大约70 ％收益率（计划3 ） 。最好使用15 5 ％
过量为了弥补一小损失的材料
由于氧化乙炔homocoupling 。逐步
进展情况反应后经1H NMR 。那个
三角连接器1的化学和热稳定性
但患有非常低溶解度hexanes ，苯，
甲苯，醚类，醇类，乙酸乙酯和乙腈;
它只有溶解在氯仿和二氯甲烷
氯化物和温和以及在DMF 。耦合
20日至23日（计划3 ） 1,3,5 triiodobenzene进行
同样。