- DMSO-Enabled Selective Radical O?H Activation of 1,3(4)-Diols
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Control of selectivity is one of the central topics in organic chemistry. Although unprecedented alkoxyl-radical-induced transformations have drawn a lot of attention, compared to selective C?H activation, selective radical O?H activation remains less explored. Herein, we report a novel selective radical O?H activation strategy of diols by combining spatial effects with proton-coupled electron transfer (PCET). It was found that DMSO is an essential reagent that enables the regioselective transformation of diols. Mechanistic studies indicated the existence of the alkoxyl radical and the selective interaction between DMSO and hydroxyl groups. Moreover, the distal C?C cleavage was realized by this selective alkoxyl-radical-initiation protocol.
- Han, Bing,Jiao, Ning,Jin, Rui,Liu, Guoquan,Liu, Jianzhong,Zhang, Ziyao,Zhu, Yuchao
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supporting information
p. 19851 - 19856
(2020/09/04)
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- Electron transfer reactions from alkali metal surfaces to (+/-) and (S)-(-)-1,3-dimethoxy-1,1-diphenylbutane. Studies on 1,3-elimination
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The 1,3-elimination of methoxide by carbanions generated from the reaction of (+/-)-1,3-dimethoxy-1,1-diphenylbutane with the alkali metals, lithium, sodium, and potassium, in various solvents was studied to determine the significance of cation-methoxyl c
- Walborsky, Harry M.,Murari, Martha Pass
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p. 2464 - 2470
(2007/10/02)
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