期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 139, 期 17, 页码 6138-6145出版社
AMER CHEMICAL SOC
DOI: 10.1021/jacs.7b00357
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资金
- Pfizer (U.K.)
- Royal Thai Government
- DPST
- EPSRC [EP/E055273/1, EP/M019195/1]
- EPSRC [EP/E055273/1, EP/M019195/1] Funding Source: UKRI
- Engineering and Physical Sciences Research Council [EP/M019195/1, EP/E055273/1] Funding Source: researchfish
The mechanism of the oxidation of arylsilanes to phenols has been investigated using F-19 NMR spectroscopy. The formation of silanols in these reactions results from a rapid background equilibrium between silanol and alkoxysilane; the relative rates of reaction of these species was evaluated by modeling of concentration profiles obtained through F-19 NMR spectroscopic reaction monitoring. Combining these results with a study of initial rates of phenol formation, and of substituent electronic effects, a mechanistic picture involving rapid and reversible formation of a pentavalent peroxide ate complex, prior to rate-limiting aryl migration, has evolved.
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