Synthesis of Cyclic Phenyl Polyynes: Ph2P-Deprotection/Intramolecular Eglington Coupling Cyclization

doi:10.6023/cjoc201708011

Chin. J. Org. Chem. ›› 2018, Vol. 38 ›› Issue (2): 519-525.DOI: 10.6023/cjoc201708011 Previous Articles Next Articles

Notes

环苯基六炔烃的制备:脱Ph₂P(O)/分子内Eglington偶联环化反应

彭丽芬^a, 张思维^a, 王丙昊^a, 寻梦硕^a, 唐子龙^a, 焦银春^a, 许新华^b

a 湖南科技大学理论有机化学与功能分子教育部重点实验室精细聚合物可控制备及功能化应用湖南省重点实验室化学化工学院湘潭 411201;
b 湖南大学化学化工学院化学生物传感与计量学国家重点实验室长沙 410082

收稿日期:2017-08-07 修回日期:2017-09-28 发布日期:2017-10-20
通讯作者: 彭丽芬, 唐子龙 E-mail:1060137@hnust.edu.cn;zltang@hnust.edu.cn
基金资助:
湖南省教育厅一般项目（No.17C0629）、湖南科技大学博士启动基金（No.E51693）、湖南科技大学理论有机化学与功能分子教育部重点实验室开放基金（No.E21630）和国家自然科学基金（No.21402048）资助项目.

Synthesis of Cyclic Phenyl Polyynes: Ph₂P-Deprotection/Intramolecular Eglington Coupling Cyclization

Peng Lifen^a, Zhang Siwei^a, Wang Binghao^a, Xun Mengshuo^a, Tang Zilong^a, Jiao Yinchun^a, Xu Xinhua^b

a Key Laboratory of Theoretical Organic Chemistry and Functional Molecule of Ministry of Education, Hunan Provincial Key Laboratory of Controllable Preparation and Functional Application of Fine Polymers, School of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Xiangtan 411201;
b State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082

Received:2017-08-07 Revised:2017-09-28 Published:2017-10-20
Contact: 10.6023/cjoc201708011 E-mail:1060137@hnust.edu.cn;zltang@hnust.edu.cn
Supported by:
Project supported by the General Project of Hunan Education Department (No. 17C0629), the Doctoral Foundation of Hunan University of Science and Technology (No. E51693), the Open Foundation of Key Laboratory of Theoretical Organic Chemistry and Functional Molecule of Ministry of Education, Hunan University of Science and Technology (No. E21630) and the National Natural Science Foundation of China (No. 21402048).

1. Synthesis of Cyclic Phenyl Polyynes: Ph₂P-Deprotection/Intramolecular Eglington Coupling Cyclization.PDF(1028KB)

Abstract

Ph₂P (O)-deprotection/intramolecular Eglington coupling cyclization, proceeding in one-pot manner, can be applied to synthesize cyclic phenyl polyynes. Compared to Micheal M. Haley's stepwise desilylation/Eglington coupling reaction, the polar Ph₂P (O) protecting group enabled facile seperation of product from remaining starting compound for their different polarity, and it also led to easy separation of target compound because the amont of by-products which showed similar R_f to target compound decreased. Furthermore, our one-pot reaction, avoiding the workup after Ph₂P (O)-deprotection and reducing losses of materials, increased the yield of cyclic aromatic polyynes. This method showed some other outstanding features including easy synthesis of intermediates and mild reaction conditions.

Key words: one-pot reaction, diphenylphosphoryl protecting group, cyclic phenyl polyyne

Cite this article

Peng Lifen, Zhang Siwei, Wang Binghao, Xun Mengshuo, Tang Zilong, Jiao Yinchun, Xu Xinhua. Synthesis of Cyclic Phenyl Polyynes: Ph₂P-Deprotection/Intramolecular Eglington Coupling Cyclization[J]. Chin. J. Org. Chem., 2018, 38(2): 519-525.

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环苯基六炔烃的制备:脱Ph₂P(O)/分子内Eglington偶联环化反应

Synthesis of Cyclic Phenyl Polyynes: Ph₂P-Deprotection/Intramolecular Eglington Coupling Cyclization

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环苯基六炔烃的制备:脱Ph2P(O)/分子内Eglington偶联环化反应