期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 141, 期 42, 页码 16643-16650出版社
AMER CHEMICAL SOC
DOI: 10.1021/jacs.9b05921
关键词
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资金
- Welch Foundation [AX-1871]
- Shenzhen Basic Research Program [JCYJ20170412150343516]
alpha-Aminoradicals undergo halogen atom abstraction to form halomethyl radicals in reactions initiated by the combination of tert-butyl hydroperoxide, aliphatic trialkyl-amine, halocarbon, and copper(I) iodide. The formation of the alpha-aminoradical circumvents preferential hydrogen atom transfer in favor of halogen atom transfer, thereby releasing the halomethyl radical for addition to alkenes. The resulting radical addition products add the tert-butylperoxy group to form alpha-peroxy-beta,beta-dichloropropylbenzene products that are convertible to their corresponding beta,-dichloro-alcohols and to novel pyridine derivatives. Computational analysis clearly explains the deviation from traditional HAT of chloroform and also establishes formal oxidative addition/reductive elimination as the lowest energy pathway.
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