Key Lab for Special Functional Materials of Ministry of Education, Henan University, Kaifeng 475004, China.
Beilstein J Org Chem. 2009 Oct 13;5:55. doi: 10.3762/bjoc.5.55.
With 3,3'-bi[benzo[b]thiophenyl] as starting material, dibenzo[d,d']benzo[1,2-b:4,3-b']dithiophene, a [5]heterohelicene, was synthesized efficiently in 60% yield via formylation and McMurry reaction. Cyclopenta[1,2-b:4,3-b']bis(benzo[d]thiophen)-6-one, another interesting helical ketone, was also prepared in 79% yield via deprotonation and ketonization of 3,3'-bi[benzo[b]thiophenyl]. In addition, the single-crystal structure of dibenzo[d,d']benzo[1,2-b:4,3-b']dithiophene and UV-vis spectra of both title compounds are described.
以 3,3'-联苯并[b]噻吩为起始原料，通过甲酰化和麦克默里反应，高效合成了[5]杂轮烯二苯并[d,d']苯并[1,2-b:4,3-b']二噻吩，产率为 60%。通过 3,3'-联苯并[b]噻吩的脱质子化和酮化反应，还以 79%的产率得到了另一种有趣的螺旋酮环戊[1,2-b:4,3-b']双（苯并[d]噻吩）-6-酮。此外，还描述了二苯并[d,d']苯并[1,2-b:4,3-b']二噻吩的单晶结构和两个标题化合物的紫外可见光谱。
