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 in | Tetrahedron letters Vol. 56; no. 4; pp. 642 - 645 |
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| Main Authors | , , , , , |
| Format | Journal Article |
| Language | English |
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Elsevier Ltd
21.01.2015
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| Abstract | [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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| AbstractList | 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. [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. |
| Author | Hess, Jeremy P. Price, John M. Adler, Marc J. Suating, Paolo Varjosaari, Sami E. Gilbert, Thomas M. |
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Synthetic organic chemists generally think of silyl ethers as easier-to-cleave alkyl ethers, frequently neglecting to consider both the... Synthetic organic chemists generally think of silyl ethers as easier-to-cleave alkyl ethers, frequently neglecting to consider both the unique facets of... |
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| SubjectTerms | Catalysis Catalysts Chemists Ethers Friedel-Crafts reaction Hydrogen bonding catalysis Silicon Spectroscopy Stereoelectronic effects Tetrahedrons Umpolung |
| Title | Stereoelectronics of silyloxybenzoic acids |
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