Stereoelectronics of silyloxybenzoic acids

[Display omitted] Synthetic organic chemists generally think of silyl ethers as easier-to-cleave alkyl ethers, frequently neglecting to consider both the unique facets of elemental silicon and the size of commonly used trialkylsilyl protecting groups. In this study, several ortho- and para-silyloxyb...

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Published inTetrahedron letters Vol. 56; no. 4; pp. 642 - 645
Main Authors Varjosaari, Sami E., Hess, Jeremy P., Suating, Paolo, Price, John M., Gilbert, Thomas M., Adler, Marc J.
Format Journal Article
LanguageEnglish
Published Elsevier Ltd 21.01.2015
Subjects
Catalysis
Catalysts
Chemists
Ethers
Friedel-Crafts reaction
Hydrogen bonding catalysis
Silicon
Spectroscopy
Stereoelectronic effects
Tetrahedrons
Umpolung
Umpolung
Stereoelectronic effects
Hydrogen bonding catalysis
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Summary:[Display omitted] Synthetic organic chemists generally think of silyl ethers as easier-to-cleave alkyl ethers, frequently neglecting to consider both the unique facets of elemental silicon and the size of commonly used trialkylsilyl protecting groups. In this study, several ortho- and para-silyloxybenzoic acids were investigated spectroscopically and as catalysts for a Friedel–Crafts reaction, with results highlighting some of the underestimated aspects of trialkylsilyloxyl substituents.
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content type line 23
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2014.12.013