Mechanistic Study of Arylsilane Oxidation through 19F NMR Spectroscopy | Zendy

Elizabeth J. Rayment | Zendy; Aroonroj Mekareeya | Zendy; Nick Summerhill | Zendy; Edward A. Anderson | Zendy

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Mechanistic Study of Arylsilane Oxidation through ¹⁹F NMR Spectroscopy

Author(s) -

Elizabeth J. Rayment,

Aroonroj Mekareeya,

Nick Summerhill,

Edward A. Anderson

Publication year - 2017

Publication title -

journal of the american chemical society

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 7.115

H-Index - 612

eISSN - 1520-5126

pISSN - 0002-7863

DOI - 10.1021/jacs.7b00357

Subject(s) - chemistry , silanol , fluorine 19 nmr , nuclear magnetic resonance spectroscopy , peroxide , substituent , phenol , phenols , reaction mechanism , spectroscopy , aryl , proton nmr , limiting , computational chemistry , photochemistry , organic chemistry , catalysis , mechanical engineering , physics , alkyl , quantum mechanics , engineering

The mechanism of the oxidation of arylsilanes to phenols has been investigated using 19 F 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 19 F 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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