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Mechanistic Studies on Propargyl Alcohol‐Tethered Alkylidenecyclopropane with Aryldiazonium Salt Initiated by Visible Light
Author(s) -
Liu Jiaxin,
Wei Yin,
Shi Min
Publication year - 2021
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.202000469
Subject(s) - chemistry , photochemistry , salt (chemistry) , deuterium , electron transfer , kinetic control , visible spectrum , redox , propargyl , triad (sociology) , combinatorial chemistry , organic chemistry , catalysis , physics , quantum mechanics , psychology , optoelectronics , psychoanalysis
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.