Singlet oxygenation of cis, cis-1,5-cyclooctadiene and thermal rearrangement of product

Acta Chimica Sinica ›› 1988, Vol. 46 ›› Issue (8): 791-795. Previous Articles Next Articles

Original Articles

顺, 顺-1,5-环辛二烯的单重态氧反应及其产物的重排

陈东立;何慧珠;李琼瑶;萧绪玲;王夺元

中国科学院感光化学研究所

发布日期:1988-08-15

Singlet oxygenation of cis, cis-1,5-cyclooctadiene and thermal rearrangement of product

CHEN DONGLI;HE HUIZHU;LI QIONGYAO;XIAO XULING;WANG DUOYUAN

Published:1988-08-15

Abstract

With hypocrellin A associated high pressure sodium lamp sensitized photooxygenation of cis,cis-1,5-cyclooctadiene in methanol gave cis-5,8-dihydroperoxyl-1,3-cyclooctadiene efficiently and stereoselectively. It is shown that cis-5,8-dihydroxy-1,3-cyclooctadiene is thermally rearranged to 6-hydroxy-4-cyclooctenone instead of 6-hydroxy-3-cyclooctenone. The thermal rearrangement process was discussed.

Key words: REARRANGEMENT REACTION, HYDROPEROXIDE P, STEREOSELECTIVITY, SODIUM LAMPS, PERICYCLIZATION, SINGLET OXYGEN, PHOTOSENSITIZER, CYCLOOCTADIENE P, CYCLOOCTADIENE P, KETENE

CLC Number:

O621.16

Cite this article

CHEN DONGLI;HE HUIZHU;LI QIONGYAO;XIAO XULING;WANG DUOYUAN. Singlet oxygenation of cis, cis-1,5-cyclooctadiene and thermal rearrangement of product[J]. Acta Chimica Sinica, 1988, 46(8): 791-795.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

[1]	Yaning Li, Xiaoyan Wang, Yong Tang. The Regulation of Stereoselectivity in Radical Polymerization^★ [J]. Acta Chimica Sinica, 2024, 82(2): 213-225.
[2]	Xin Lv, Yi Wu, Boran Zhang, Wei Guo. Design, Synthesis and Photodynamic Therapy of a H₂O₂-Activatable Near Infrared Borondipyrromethene （BODIPY） Photosensitizer [J]. Acta Chimica Sinica, 2023, 81(4): 359-370.
[3]	Yinghong Yan, Pingzhao Liang, Yang Zou, Lin Yuan, Xiaojun Peng, Jiangli Fan, Xiaobing Zhang. Structure and Properties Regulation of Organic Photosensitizers and Application in Photodiagnosis and Treatment^★ [J]. Acta Chimica Sinica, 2023, 81(11): 1642-1662.
[4]	Xiaojuan Li, Ziyu Ye, Shuhan Xie, Yongjing Wang, Yonghao Wang, Yuancai Lv, Chunxiang Lin. Study on Performance and Mechanism of Phenol Degradation through Peroxymonosulfate Activation by Nitrogen/Chlorine Co-doped Porous Carbon Materials [J]. Acta Chimica Sinica, 2022, 80(9): 1238-1249.
[5]	Badi Liu, Chengjun Wang, Ying Qian. Synthesis, Two-photon Fluorescence Imaging and Photodynamic Therapy of Near Infrared Thienyl-BODIPY Photosensitizer [J]. Acta Chimica Sinica, 2022, 80(8): 1071-1083.
[6]	Yunfang Xu, Yang Li, Zitong Fu, Shaoyan Lin, Jie Zhu, Lei Wu. Palladium-catalyzed Stereoselective Synthesis of (Z)-[3]Dendralenes [J]. Acta Chimica Sinica, 2022, 80(10): 1369-1375.
[7]	He Tong, Yang Xiaofeng, Chen Yuzhe, Tong Zhenhe, Wu Lizhu. Triplet-Triplet Annihilation Upconversion Based on Silica Nanoparticles [J]. Acta Chim. Sinica, 2019, 77(1): 41-46.
[8]	Li Shu-Sen, Wang Jianbo. Recent Advance in Asymmetric Trifluoromethylthiolation [J]. Acta Chim. Sinica, 2018, 76(12): 913-924.
[9]	Li Mingle, Peng Xiaojun. Research Progress on the Phthalocyanine Based Targeting Photosensitizers in Photodynamic Therapy [J]. Acta Chim. Sinica, 2016, 74(12): 959-968.
[10]	Long Saran, Wan Yan, Xia Andong. Spectral Properties of Water-Soluble Conjugated Polymer PFP/DNA/Porphyrin Complex [J]. Acta Chim. Sinica, 2015, 73(7): 723-728.
[11]	Zhou Rong, Xiao Wei, Yin Xiang, Zhan Gu, Chen Yingchun. Diastereo- and Enantioselective [4+2] Cycloadditions of Cyclic Enones with Cyclic 1-Azadienes [J]. Acta Chimica Sinica, 2014, 72(7): 862-866.
[12]	LI Mei-Rong, CAI Xiao-Qing, ZHU Yi-Feng, LIU Kuan-Guan, HU Mao-Lin. Synthesis and Biological Evaluation of Novel Coupling Derivatives of Photosensitizer and 5-fluorouracil as Antineoplastic Agents [J]. Acta Chimica Sinica, 2011, 69(04): 425-430.
[13]	NA Lu-Xin, ZHAO Dong-Mei, SONG Shuai, SUN Liang, CHENG Mao-Sheng. Stereochemistry of Narcotine and Phthalideisoquinoline Synthesized via Bischler-Napieralski Reaction [J]. Acta Chimica Sinica, 2011, 69(03): 356-361.
[14]	HUANG Qi-Mao, DENG Peng-Xing, LI Zhi-Yuan, ZHOU Hong, HU Xue-Lei, PAN Zhi-Quan. Synthesis of Novel β-Substituted Cationic Porphyrins as Photosensitizer and Their Interactions with DNA [J]. Acta Chimica Sinica, 2010, 68(11): 1070-1076.
[15]	LI Hui-Hua, LI Zhi-Feng, WANG Xiao-Feng, DONG Xiao-Ning, SHU Yuan-Cheng. Theoretical Study on the Multi-channel Reaction Mechanism of CH₂CO＋CH₂ [J]. Acta Chimica Sinica, 2010, 68(02): 115-124.

顺, 顺-1,5-环辛二烯的单重态氧反应及其产物的重排

Singlet oxygenation of cis, cis-1,5-cyclooctadiene and thermal rearrangement of product

PDF

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments