4.5 Article

Mechanistic Studies on Propargyl Alcohol-Tethered Alkylidenecyclopropane with Aryldiazonium Salt Initiated by Visible Light

期刊

CHINESE JOURNAL OF CHEMISTRY
卷 39, 期 2, 页码 295-300

出版社

WILEY-V C H VERLAG GMBH
DOI: 10.1002/cjoc.202000469

关键词

Mechanistic study; Photochemistry; Radical ion; Spirobi[indene]; Radical chain

资金

  1. Strategic Priority Research Program of the Chinese Academy of Sciences [XDB20000000]
  2. National Natural Science Foundation of China [21421091, 21372250, 21121062, 21302203, 20732008, 21772037, 21772226, 21861132014, 91956115]

向作者/读者索取更多资源

This study reveals the reaction mechanisms of two consecutive visible light photo-induced chain processes, triggered by photo-induced single-electron transfer and direct SET processes respectively. These processes were supported by mechanistic studies and experiments to achieve a redox-neutral outcome.
Main observation and conclusion This paper discloses the reaction mechanism of two consecutive but different visible light photo-induced chain processes for the rapid construction of spirobi[indene] skeletons. The first process is triggered by a photo-induced single-electron-transfer (SET) of an electron donor-accepter (EDA) complex. The second process is initiated by a direct SET process between aryldiazonium salt and the excited allenic intermediate. In these two processes, another SET took place respectively on the in situ formed radical intermediate to realize a redox-neutral outcome. The mechanistic studies have been carried out by control experiments, kinetic and spectroscopic analyses, deuterium labeling experiments to support these two chain processes. [GRAPHICS] .

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